Crystalline forms of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazine-4-yl]-5-(2-chloro-4-methylbenzyl)-5, 6-dihydro-4H-1, 2, 4-oxadiazine

Abstract

The present invention relates to a novel crystalline form of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazine-4-yl]-5-(2-chloro-4-methylbenzyl)-5, 6-dihydro-4H-1, 2, 4-oxadiazine of formula (I), to a process for the preparation thereof, to agrochemical formulations comprising this novel crystalline form, and to the use thereof in plant protection applications, in particular as a fungicide (I). # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a new crystal form of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine of formula (I), a preparation method thereof, an agrochemical preparation containing the new crystal form B and the use thereof in plant protection applications, in particular to the use thereof as a fungicide.

[0002]

[0003] (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine and its preparation method are known from WO 2020 / 127780. (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine obtained by the method known in the prior art is an amorphous solid. Background Art

[0004] Polymorphism is the ability of a compound to crystallize in different crystalline phases with different molecular arrangements and / or conformations in the crystal lattice. Therefore, polymorphs are different crystal forms of the same chemical compound. Due to the different arrangements and / or conformations of molecules, polymorphs can exhibit different physical, chemical and / or biological properties. The properties that can be affected include but are not limited to solubility, dissolution rate, stability, optical properties and mechanical properties. The relative stability of polymorphs depends on their free energy, i.e., more stable polymorphs have lower free energy. Under a set of determined experimental conditions, only one polymorph has the lowest free energy. This polymorph is a thermodynamically stable form, and all other polymorphs are referred to as metastable forms. Metastable forms are forms that are thermodynamically unstable but can still be prepared, separated and analyzed due to their relatively slow conversion rates.

[0005] The occurrence of different polymorphic forms (also referred to herein as polymorphs or crystalline forms) of an active substance is crucial for the industrial-scale preparation and development of formulations containing the active substance, since undesired phase changes can lead to thickening and potential solidification of the formulation and / or large crystals, which can lead to clogging of application equipment (e.g. nozzles in agricultural application machinery). Therefore, knowledge of the presence of crystalline modifications and their properties is highly relevant. Each polymorph is characterized by a specific, uniform packing and arrangement of molecules in the solid state. However, it is generally completely impossible to predict whether a given chemical compound forms polymorphs, and if so, which physical and biological properties the different polymorphs may have.

[0006] In addition, there can be pseudopolymorphs known as hydrates or solvates. Solvates are crystallized molecular compounds in which molecules of the crystallization solvent are incorporated into a host lattice consisting of unsolvated molecules. Hydrates are a special case of solvates, in which the incorporated solvent is water. The presence of solvent molecules in the lattice affects the intermolecular interactions and gives each solvate unique physical properties. Therefore, solvates have their own characteristic values ​​for internal energy, enthalpy, entropy, Gibbs free energy, and thermodynamic activity. BRIEF DESCRIPTION OF THE DRAWINGS

[0007] Figure 1a: X-ray powder diffraction pattern of polymorph B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine.

[0008] Figure 1b: FT Raman spectrum of polymorph B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine.

[0009] Figure 1c: IR spectrum of polymorph B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine.

[0010] Figure 2a: X-ray powder diffraction pattern of polymorph A of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine.

[0011] Figure 3a: X-ray powder diffraction pattern after slurry experiment 3 (8d / 80°C CH3CN / H2O). DETAILED DESCRIPTION

[0012] In one embodiment, the present invention relates to a novel crystalline form B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine of formula (I),

[0013]

[0014] The process according to WO 2020 / 127780 gives the unwanted amorphous form of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine.

[0015] It is therefore an object of the present invention to provide a polymorph having excellent administration properties, in particular excellent physiochemical properties, such as high stability in suspension concentrate (SC) formulations.

[0016] The compound of formula (I) crystallizes in two modifications, A and B. Polymorphs A and B are enantiomerically related, exhibiting a critical transition temperature between 49° C. and 66° C. This temperature range can be reached during the preparation process and can lead to a solid-solid transformation from polymorph B to polymorph A, which can recrystallize to form B at room temperature, thereby inducing agglomeration in solid-based formulation types.

[0017] It has now been surprisingly found that polymorph B of the compound of formula (I) has excellent properties. Compared with the amorphous form known in the prior art, polymorph B exhibits improved beneficial properties for preparing formulations. In particular, polymorph B exhibits high stability in suspension concentrate (SC) formulations, such as high dilution stability, especially suspension, thereby ensuring that it is prevented from being undesirably converted into another polymorph of the compound of formula (I). Known polymorph transitions are expected to lead to instability in SC formulations (J. Weiss et al., J. Am. Oil Chem. Soc. 2008, 85, 501-511; DJ Burgess et al., Int. J. Pharmaceutics, 2014, Vol. 466, 223-232), such as particle aggregation leading to lower suspension. In addition, polymorph B exhibits surprisingly high stability in slurry experiments conducted over a long period of time above the transition temperature range. No recrystallization phenomenon was observed. High stability ensures that relevant changes in the above-mentioned properties will not occur, and thus improves the safety and quality of the formulations and / or compositions comprising the polymorph B of the compound of formula (I).

[0018] The polymorphic form B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine can be characterized by X-ray powder diffraction based on the corresponding diffraction pattern recorded at 25° C. using Cu-Kα1 radiation. The polymorph B of the invention exhibits at least 3, generally at least 5, in particular at least 7, more in particular at least 10 and especially all the reflections cited below with values:

[0019] Table 1: X-ray reflections of polymorph B

[0020] Reflection [2θ value] x±0.2° 5.3 6.7 8.5 10.6 14.5 15.8 17.2 19.0 19.4 20.2 21.1 22.1 22.7 22.9 23.3 24.2 25.1 26.6 27.3 27.7 29.0 29.2 31.1 31.5 32.0 32.4 33.1 34.3 35.0

[0021] The polymorph B of the present invention is further characterized by the X-ray powder diffraction pattern shown in Figure 1a.

[0022] Polymorph B of the compound of formula (I) is characterized in that the X-ray powder diffraction pattern using Cu-Kα1 radiation at 25°C has at least the following reflections: 20.2, 23.3 and 25.1, preferably at least the following reflections: 20.2, 23.3, 25.1, 14.5 and 19.4, more preferably at least the following reflections: 20.2, 23.3, 25.1, 14.5, 19.4, 23.4 and 10.6.

[0023] The polymorph B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine can also be characterized by Raman spectroscopy based on the corresponding spectra recorded at 25° C. using a laser wavelength of 1064 nm and 2 cm -1 The polymorph B of the invention exhibits at least 3, generally at least 5, in particular at least 7, and especially all the bands cited below as peak maxima:

[0024] Table 2: Raman bands of type B

[0025]

[0026]

[0027] Polymorph B of the compound of formula (I) is characterized by the following bands: 98, 112 and 1585, preferably at least the following bands: 98, 112, 1585, 1279 and 2925, more preferably at least the following bands: 98, 112, 1585, 1279, 2925, 688 and 1609.

[0028] The polymorphic form B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine can also be characterized by infrared spectroscopy based on the corresponding spectra recorded at 25° C. using a universal diamond ATR apparatus and 2 cm -1The polymorph B of the invention exhibits at least 3, generally at least 5, in particular at least 7, and especially all the bands cited below as peak maxima:

[0029] Table 3: IR bands of Form B

[0030]

[0031]

[0032] Polymorph B of the compound of formula (I) is characterized by the following bands: 1403, 819 and 806, preferably at least the following bands: 1403, 819, 806, 1476 and 1274, more preferably at least the following bands: 1403, 819, 806, 1476, 1274, 1383 and 921.

[0033] In addition to polymorph B, another polymorph A was identified (Fig. 2a), which is further characterized below.

[0034] In one embodiment, the present invention relates to a new crystalline form A of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine of formula (I),

[0035]

[0036] The polymorphic form A of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine can be characterized by X-ray powder diffraction based on the corresponding diffraction pattern recorded at 25° C. using Cu-Kα1 radiation. Polymorph A exhibits at least 3, generally at least 5, in particular at least 7, more in particular at least 10 and especially all the reflections cited below with values:

[0037] Table 4: X-ray reflections of polymorph A

[0038]

[0039]

[0040] Polymorph A of the compound of formula (I) is characterized in that the X-ray powder diffraction pattern using Cu-Kα1 radiation at 25°C has at least the following reflections: 16.9, 19.8 and 24.5, preferably at least the following reflections: 16.9, 19.8, 24.5, 14.2 and 24.7, more preferably at least the following reflections: 16.9, 19.8, 24.5, 14.2, 24.7, 20.8 and 21.8, more preferably at least the following reflections: 16.9, 19.8, 24.5, 14.2, 24.7, 20.8, 21.8, 38.9, 38.3 and 29.5, each quoted as a 2θ value ±0.2°.

[0041] Polymorph A is further characterized by the X-ray powder diffraction pattern shown in Figure 2a.

[0042] The thermodynamic stability of polymorphs A and B is highly complex. The two forms are enantiomerically related and have transition temperatures ranging from 49° C. to 66° C. Below these temperatures, polymorph B is the thermodynamically stable polymorph. Polymorph A recrystallizes at higher temperatures, but exhibits a very rapid transition to polymorph B at lower temperatures.

[0043] In yet another embodiment, the present invention relates to a process for preparing polymorph B comprising the following steps:

[0044] a) diluting the compound of formula (I) in a suitable solvent or solvent mixture,

[0045] b) heating the composition of step a) to a temperature of at least 70° C., and

[0046] c) cooling the solution from step b) to a temperature below 20°C.

[0047] The chemical preparation of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine of formula (I) is known from WO 2020 / 127780. Therefore, the compound of formula (I) used in step a) can be prepared according to WO 2020 / 127780, which is hereby fully cited.

[0048] The compound of formula (I) in step a) can be essentially any known form of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine. This means that (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine can be used in amorphous form or as a mixture of different polymorphs or as a mixture containing an amorphous form and one or more different polymorphs.

[0049] Suitable solvents or solvent mixtures which can be used to dilute and / or suspend the compound of formula (I) in step a) and from which the compound of formula (I) is obtained in polymorph B in step c) are toluene, tetrahydrofuran, acetone, ethyl acetate, acetonitrile, methanol, ethanol, isopropanol, N,N-dimethylformamide, 1,4-dioxane or DMSO, preferably toluene, ethanol or 1,4-dioxane.

[0050] A solution of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine can also be prepared by transferring the reaction mixture obtained by the chemical reaction containing (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine, if necessary after removing reagents and / or by-products, to a solvent or solvent mixture of the present invention.

[0051] In step b), the solution or slurry is generally heated to a temperature of at least 70° C., preferably to a temperature of at least 90° C. In a preferred embodiment, each solvent or solvent mixture is heated to its boiling temperature.

[0052] In step c), the solution or slurry is cooled to a temperature below 20°C, preferably below 0°C.

[0053] Crystallization of polymorph Form B may be promoted or accelerated by seeding with Form B seed crystals.

[0054] Polymorph B is isolated from the mother liquor by conventional techniques known in the art, for example by filtration, centrifugation or decantation.

[0055] More preferably, polymorph B is isolated from the solvent or solvent mixture by allowing the solution or slurry to stand under the crystallization conditions of step c) until at least 90% by weight of the solvent or solvent mixture has evaporated.

[0056] The isolated polymorph B can optionally be washed with any solvent, preferably with the solvent or solvent mixture used for crystallization, with water or with a mixture of a solvent or solvent mixture and water. The washing step can optionally be repeated, whereby washing with water is usually the last washing step. Washing is usually carried out at below 30° C., usually below 25° C., in particular below 20° C., optionally at 0° C. In a further optional step, the crystals of polymorph B can be dried and then provided for further processing.

[0057] By the crystallization of the present invention, form B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine is obtained in an amount of at least 85%, particularly 90%, and most preferably at least ≥95%.

[0058] Therefore, a specific embodiment of the present invention relates to (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine, which consists of at least 85% and typically at least 90% or at least ≥95% of polymorph B.

[0059] In another embodiment, the present invention relates to a plant protection agent in the form of a conventional formulation containing polymorph B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine.

[0060] In a preferred embodiment of the invention, the crop protection agent contains more than 90% by weight and preferably more than 95% by weight of polymorph B of the compound of the formula (I), based on the total amount of all forms of the compound of the formula (I) present in the composition.

[0061] Surprisingly, it has now been found that polymorph B has improved handling and formulation properties, such as high stability of SC formulations, such as high dilution stability, in particular high suspension properties, in particular at higher temperatures, even above the transition temperature range. Therefore, in another embodiment, the present invention relates to the use of polymorph B of a compound of formula (I) for the preparation of formulations having high stability, preferably high dilution stability, more preferably high suspension properties, in particular at temperatures above the transition temperature range.

[0062] use

[0063] In another embodiment, the present invention relates to the use of polymorph B of the compound of formula (I) for controlling unwanted microorganisms, preferably unwanted fungi and viruses. In a specific embodiment, the present invention relates to controlling unwanted fungi on plants. In a specific embodiment of the present invention, the useful plants are transgenic plants.

[0064] In another embodiment, the invention relates to a method for controlling unwanted microorganisms, wherein the polymorph B or a plant protection agent containing the polymorph B as defined above is applied to plants.

[0065] The compounds and compositions of the present invention have potential microbicidal activity and / or plant defense regulation potential. They can be used to control unwanted microorganisms on plants, such as unwanted fungi and viruses. They can be used in particular for crop protection (they control microorganisms that cause plant diseases) or for protecting materials (e.g. industrial materials, timber, stored goods) described in more detail below. More specifically, the compounds of the present invention and the compositions of the present invention can be used to protect seeds, germinating seeds, newly emerging seedlings, plants, plant parts, fruits, harvested articles and / or soil in which plants grow from attack by unwanted microorganisms.

[0066] Described in this article Prevention (Control or controlling) includes the prevention, treatment and elimination of unwanted microorganisms. Unwanted microorganisms It can be a pathogenic virus or a pathogenic fungus, more specifically a plant pathogenic virus or a plant pathogenic fungus. As described in detail below, these plant pathogenic microorganisms are the causative agents of a wide spectrum of plant diseases.

[0067] More specifically, the compounds according to the invention and the compositions according to the invention can be used as fungicides. For the purposes of the present invention, the term "fungicide" refers to compounds or compositions which can be used in crop protection to control unwanted fungi, such as Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

[0068] The compounds and compositions according to the invention can also be used as antiviral agents in crop protection. For example, the compounds and compositions of the present invention can have an effect on diseases caused by plant viruses, such as tobacco mosaic virus (TMV), tobacco rattle virus, tobacco stunt virus (TStuV), tobacco leaf curl virus (VLCV), tobacco nervilia mosaic virus (TVBMV), tobacco necrotic dwarf virus (TNDV), tobacco streak virus (TSV), potato virus X (PVX), potato viruses Y, S, M and A, potato acubamosaic virus (PAMV), potato mop-top virus (PMTV), potato leaf-roll virus (PLRV), alfalfa mosaic virus ( virus (AMV), cucumber mosaic virus (CMV), cucumber green mottle mosaic virus (CGMMV), cucumber yellows virus (Cucumber yellows virus) ...virus) (SMYEV), strawberry crinkle virus (SCrV), broad bean wilt virus (BBWV), and melon necrotic spot virus (MNSV).

[0069] The present invention also relates to a method for controlling unwanted microorganisms (such as unwanted fungi) on plants, which comprises the step of applying polymorph B of the compound of formula (I) according to the present invention or at least one composition according to the present invention to the microorganisms and / or their habitat (to plants, plant parts, seeds, fruits or to the soil in which the plants grow).

[0070] In general, when the compounds and compositions of the invention are used in a curative or protective method for controlling phytopathogenic fungi, they are applied in an effective and phytocompatible amount to plants, plant parts, fruits, seeds or to the soil or substrate in which the plants grow. Suitable substrates for cultivating plants include inorganic-based substrates, such as mineral wool, especially asbestos, perlite, sand or gravel; organic substrates, such as peat, pine bark or sawdust; and petroleum-based substrates, such as polymer foams or plastic beads. Effective and plant-compatible amount It means an amount sufficient to control or destroy fungi present or susceptible to occur on agricultural land without causing any obvious phytotoxic symptoms in the crop. The amount may vary within a wide range, depending on the fungi to be controlled, the type of crop, the growth stage of the crop, the climatic conditions and the individual compounds or compositions of the invention used. The amount may be determined by systematic field trials and is within the capabilities of those skilled in the art.

[0071] Plants and plant parts

[0072] The compounds and compositions of the present invention may be applied to any plant or plant part.

[0073] plant This means all plants and plant populations, for example desired and unwanted wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnology and genetic engineering methods or a combination of these methods, including genetically modified plants (GMO or transgenic plants) and plant cultivars which are or are not protected by plant breeders' rights.

[0074] Plant cultivarsIt is to be understood as meaning plants which have new properties ("traits") and which have been obtained by conventional breeding, mutagenesis or recombinant DNA techniques. They may be cultivars, varieties, biotypes or genotypes.

[0075] Plant parts It should be understood as meaning all parts and organs of the plant above and below the ground, such as buds, leaves, needles, stems, trunks, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. Plant parts also include harvested material and asexual and sexual propagation material, for example cuttings, tubers, rhizomes, divisions and seeds.

[0076] Plants and plant parts

[0077] The compounds and compositions of the present invention may be applied to any plant or plant part.

[0078] plant This means all plants and plant populations, for example desired and unwanted wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnology and genetic engineering methods or a combination of these methods, including genetically modified plants (GMO or transgenic plants) and plant cultivars which are or are not protected by plant breeders' rights.

[0079] Plant cultivars It is to be understood as meaning plants which have new properties ("traits") and which have been obtained by conventional breeding, mutagenesis or recombinant DNA techniques. They may be cultivars, varieties, biotypes or genotypes.

[0080] Plant parts It should be understood as meaning all parts and organs of the plant above and below the ground, such as buds, leaves, needles, stems, trunks, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. Plant parts also include harvested material and asexual and sexual propagation material, for example cuttings, tubers, rhizomes, divisions and seeds.

[0081] Plants that can be treated according to the methods described herein include the following: cotton, flax, grapevines, fruits, vegetables, such as Rosaceae sp. (e.g., pome fruits, such as apples and pears, and stone fruits, such as apricots, cherries, almonds and peaches, and small fruit, such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (e.g., banana trees and banana plantations), Rubiaceae sp. (e.g., coffee), Theaceae sp., Sterculiceae sp. sp.), Rutaceae sp. (e.g. lemon, orange and grapefruit), Solanaceae sp. (e.g. potato and tomato), Liliaceae sp., Asteraceae sp. (e.g. lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (e.g. cucumber), Alliaceae sp. (e.g. leek, onion), Papilionaceae sp. (e.g. pea); major crop plants, such as Gramineae sp. (e.g. corn, lawn grass, cereals (e.g. wheat, rye, rice, barley, oats, millet and triticale)), Asteraceae sp. (e.g. sunflower), Brassicaceae sp. sp.) (e.g. white cabbage, red cabbage, Brussels sprouts, cauliflower, Brussels sprouts, pakchoi, kohlrabi, radish, as well as rapeseed, mustard, horseradish and watercress), Fabacae sp. (e.g. beans, peanuts), Papilionaceae sp. (e.g. soybeans), Chenopodiaceae sp. (e.g. sugar beets, fodder beets, Swiss chard, beetroot); useful plants and ornamental plants for gardens and forests; and genetically modified variants of each of these plants.

[0082] Plants and plant cultivars which can be treated by the methods disclosed above include plants and plant cultivars which are resistant to one or more biotic stresses, ie the plants have an improved defense against animal or microbial pests (e.g. against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids).

[0083] Plants and plant cultivars that can be treated by the above disclosed methods include those plants that are resistant to one or more abiotic stresses. Abiotic stress conditions can include, for example, drought, low temperature exposure, heat exposure, osmotic stress, waterlogging, increased soil salinity, enhanced mineral exposure, ozone exposure, high light exposure, limited nitrogen nutrient availability, limited phosphorus nutrient availability, and shade avoidance.

[0084] Plants and plant cultivars that can be processed by the above-mentioned disclosed method include those plants characterized by the yield characteristics of improvement. The yield improved in the plant can be the result of the following factors: for example, improved plant physiology, growth and development, such as water use efficiency, water holding efficiency, improved nitrogen utilization rate, enhanced carbon assimilation, improved photosynthesis, improved germination rate and accelerated maturity. Yield can also be affected by improved plant architecture (plant architecture) (under stress and non-stress conditions), and the plant architecture includes but is not limited to: early flowering, flowering control of hybrid seed production, rice seedling vigor, plant size, internode number and internode distance, root growth, seed size, fruit size, pod size, pod number or ear number, seed quantity of each pod or ear, seed quality, enhanced seed fullness, reduced seed dispersal, reduced pod cracking and lodging resistance. Other yield traits include seed composition, such as carbohydrate content and composition, for example cotton or starch, protein content, oil content and composition, nutritional value, anti-nutritional compounds reduction, improved processability and better storage stability.

[0085] Plants and plant cultivars that may be treated by the above disclosed methods include plants and plant cultivars that are hybrid plants that already express the characteristic of heterosis or hybrid vigour, which generally results in higher yield, vigour, health and resistance to biotic and abiotic stresses.

[0086] Transgenic plants, seed treatments and integrated lines (event)

[0087] The polymorphic form B of the compound of formula (I) of the present invention can be advantageously used to treat transgenic plants, plant cultivars or plant parts that have received genetic material that imparts favorable and / or useful properties (traits) to these plants, plant cultivars or plant parts. Therefore, it is contemplated that the present invention is combined with one or more recombinant traits or transgenic lines (transgenic event) or a combination thereof. For the purposes of this application, transgenic lines are produced by inserting specific recombinant DNA molecules into specific locations (sites) of plant genome chromosomes. The insertion creates a new DNA sequence called a "line", characterized in that the inserted recombinant DNA molecules and a certain amount of genomic DNA are adjacent to both ends of the inserted DNA / side the two ends of the inserted DNA. Such traits or transgenic lines include, but are not limited to, resistance to pests and diseases, water use efficiency, yield performance, drought tolerance, seed quality, improved nutritional quality, hybrid seed production and herbicide tolerance, wherein the trait is determined relative to a plant lacking such a trait or transgenic line. Specific examples of such advantageous and / or useful properties (traits) are better plant growth, vigor, stress tolerance, stand growth ability, lodging resistance, nutrient uptake, plant nutrition and / or yield, in particular improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salinity levels, enhanced flowering performance, easier harvesting, accelerated maturation, higher yield, higher quality and / or higher nutritional value of the harvested product, better storage life and / or processability of the harvested product, and increased resistance to animal and microbial pests (e.g. insects, arachnids, nematodes, mites, slugs and snails).

[0088] Among the DNA sequences encoding proteins that confer tolerance traits on these animal or microbial pests, in particular insects, mention will be made in particular of the genetic material consisting of Bacillus thuringiensis encoding Bt proteins, which are well described in the literature and are well known to those skilled in the art. Mention will also be made of proteins extracted from bacteria, such as Photorhabdus (WO 97 / 17432 and WO 98 / 08932). In particular, mention will be made of the genetic material consisting of Bt proteins, which are well described in the literature and are well known to those skilled in the art. Cry or VIP proteins including Cry1A, CryIAb, CryIAc, CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF proteins or toxic fragments thereof, and hybrids or combinations thereof, in particular Cry1F protein or hybrids derived from Cry1F protein (such as hybrid Cry1A-Cry1F protein or toxic fragments thereof), Cry1A-type protein or toxic fragments thereof, preferably Cry1Ac protein or hybrids derived from Cry1Ac protein (such as hybrid Cry1Ab-Cry1Ac protein) or Cry1Ab or Bt2 protein or toxic fragments thereof, Cry2Ae, Cry2Af or Cry2Ag protein or toxic fragments thereof, Cry1A.105 protein or toxic fragments thereof, VIP3Aa19 protein, VIP3Aa20 protein, VIP3A protein produced in COT202 or COT203 cotton strains, as described in Estruch et al. (1996), Proc Natl Acad Sci US A.28; 93 (11): 5389-94 or a toxic fragment thereof, a Cry protein described in WO2001 / 47952, an insecticidal protein from Xenorhabdus (such as described in WO98 / 50427), Serratia (especially from S. entomophila) or a Photorhabdus species strain, such as the Tc protein from Photorhabdus described in WO98 / 08932. In addition, the present invention also includes all variants or mutants of any of the above proteins that differ from any of the above-listed sequences (especially the sequences of their toxic fragments) in some amino acids (1-10, preferably 1-5), or any variant or mutant of the above proteins fused with a transit peptide (such as a plastid transit peptide) or another protein or peptide.

[0089] Another and particularly emphasized example of such a property is the conferring of tolerance to one or more herbicides, such as imidazolinones, sulfonylureas, glyphosate or glufosinate. Among the DNA sequences encoding proteins conferring tolerance to certain herbicides on transformed plant cells and plants, the bar or PAT genes or the Streptomyces coelicolor genes described in WO 2009 / 152359 conferring tolerance to the glufosinate herbicide, suitable EPSPS (5-enolpyruvylshikimate-3-phosphate-synthase) genes encoding conferring tolerance to herbicides targeting EPSPS, in particular to herbicides such as glyphosate and its salts, genes encoding glyphosate-n-acetyltransferase, or genes encoding glyphosate oxidoreductase, will be mentioned in particular. Other suitable herbicide tolerance traits include at least one ALS (acetolactate synthase) inhibitor (e.g., WO2007 / 024782), a mutated Arabidopsis ALS / AHAS gene (e.g., U.S. Pat. No. 6,855,533), a gene encoding a 2,4-D-monooxygenase conferring tolerance to 2,4-D (2,4-dichlorophenoxyacetic acid), a gene encoding a Dicamba monooxygenase conferring tolerance to Dicamba (3,6-dichloro-2-methoxybenzoic acid).

[0090] Yet another example of such a property is resistance to one or more phytopathogenic fungi, such as Asian Soybean Rust. Among the DNA sequences encoding proteins conferring resistance to such diseases, mention will be made in particular of genetic material from glycine tomentella, such as any one of the publicly available registration series described in WO2019 / 103918: PI441001, PI483224, PI583970, PI446958, PI499939, PI505220, PI499933, PI441008, PI505256 or PI446961.

[0091] Further and particularly emphasized examples of such traits are increased resistance to bacteria and / or viruses due to, for example, systemic acquired resistance (SAR), systemin, phytoalexins, inducers and resistance genes and correspondingly expressed proteins and toxins.

[0092] Particularly useful transgenic lines among the transgenic plants or plant cultivars that can be preferentially treated according to the present invention include line 531 / PV-GHBK04 (cotton, insect control, described in WO2002 / 040677), line 1143-14A (cotton, insect control, not deposited, described in WO2006 / 128569); line 1143-51B (cotton, insect control, not deposited, described in WO2006 / 128570); line 1445 (cotton, herbicide tolerance, not deposited, described in US-A 2002-120964 or WO2002 / 034946); Line 17053 (rice, herbicide tolerant, deposited as PTA-9843, described in WO2010 / 117737); Line 17314 (rice, herbicide tolerant, deposited as PTA-9844, described in WO2010 / 117735); Line 281-24-236 (cotton, insect control-herbicide tolerant, deposited as PTA-6233, described in WO2005 / 103266 or US-A2005-216969); Line 3006-210-23 (cotton, insect control-herbicide tolerant, deposited as PTA-6233, described in US-A 2007-143876 or WO2005 / 103266); Line 3272 (maize, quality traits, deposited as PTA-9972, described in WO2006 / 098952 or US-A 2006-230473); Line 33391 (wheat, herbicide tolerance, deposited as PTA-2347, described in WO2002 / 027004), Line 40416 (maize, insect control-herbicide tolerance, deposited as ATCC PTA-11508, described in WO 11 / 075593); Line 43A47 (maize, insect control-herbicide tolerance, deposited as ATCC PTA-11509 deposited and described in WO2011 / 075595); Line 5307 (corn, insect control, deposited as ATCC PTA-9561, described in WO2010 / 077816); Line ASR-368 (bent grass, herbicide tolerant, deposited as ATCC PTA-4816, described in US-A 2006-162007 or WO2004 / 053062); Line B16 (corn, herbicide tolerant, not deposited, described in US-A 2003-126634); line BPS-CV127-9 (soybean, herbicide tolerance, deposited as NCIMB No. 41603, described in WO2010 / 080829); line BLR1 (rapeseed, restored male sterility, deposited as NCIMB No. 41193, described in WO2005 / 074671), line CE43-67B (cotton,insect control, deposited as DSMACC2724, described in US-A 2009-217423 or WO2006 / 128573); strain CE44-69D (cotton, insect control, not deposited, described in US-A 2010-0024077); strain CE44-69D (cotton, insect control, not deposited, described in WO2006 / 128571); strain CE46-02A (cotton, insect control, not deposited, described in WO2006 / 128572); strain COT102 (cotton, insect control, not deposited, described in US-A 2006-130175 or WO2004 / 039986); strain COT202 (cotton, insect control, not deposited, described in US-A 2007-067868 or WO2005 / 054479); line COT203 (cotton, insect control, not deposited, described in WO2005 / 054480); line DAS21606-3 / 1606 (soybean, herbicide tolerance, deposited as PTA-11028, described in WO2012 / 033794), line DAS40278 (corn, herbicide tolerance, deposited as ATCC PTA-10244 deposited, described in WO2011 / 022469); line DAS-44406-6 / pDAB8264.44.06.1 (soybean, herbicide tolerance, deposited as PTA-11336, described in WO2012 / 075426), line DAS-14536-7 / pDAB8291.45.36.2 (soybean, herbicide tolerance, deposited as PTA-11335, described in WO2012 / 075429), line DAS-59122-7 (corn, insect control-herbicide tolerance, deposited as ATCC PTA 11384, described in US-A 2006-070139); line DAS-59132 (corn, insect control-herbicide tolerance, not deposited, described in WO2009 / 100188); line DAS68416 (soybean, herbicide tolerance, deposited as ATCC PTA-10442, described in WO2011 / 066384 or WO2011 / 066360); line DP-098140-6 (corn, herbicide tolerance, deposited as ATCC PTA-8296, described in US-A 2009-137395 or WO 08 / 112019); line DP-305423-1 (soybean, quality traits, not deposited, described in US-A 2008-312082 or WO2008 / 054747); strain DP-32138-1 (maize, hybrid system, deposited as ATCC PTA-9158,09-0210970 or WO2009 / 103049); line DP-356043-5 (soybean, herbicide tolerant, deposited as ATCC PTA-8287, described in US-A 2010-0184079 or WO2008 / 002872); line EE-I (eggplant, insect control, not deposited, described in WO 07 / 091277); line Fil17 (maize, herbicide tolerant, deposited as ATCC 209031, described in US-A 2006-059581 or WO 98 / 044140); line FG72 (soybean, herbicide tolerant, deposited as PTA-11041, described in WO2011 / 063413), line GA21 (maize, herbicide tolerant, deposited as ATCC 209033, described in US-A2005-086719 or WO 98 / 044140); line GG25 (maize, herbicide tolerant, deposited as ATCC 209032, described in US-A 2005-188434 or WO 98 / 044140); line GHB119 (cotton, insect control-herbicide tolerant, deposited as ATCC PTA-8398, described in WO2008 / 151780); line GHB614 (cotton, herbicide tolerant, deposited as ATCC PTA-6878 deposited, recorded in US-A 2010-050282 or WO 2007 / 017186); line GJ11 (maize, herbicide tolerant, deposited as ATCC 209030, recorded in US-A 2005-188434 or WO 98 / 044140); line GM RZ13 (sugar beet, virus resistant, deposited as NCIMB-41601, recorded in WO 2010 / 076212); line H7-1 (sugar beet, herbicide tolerant, deposited as NCIMB 41158 or NCIMB 41159, recorded in US-A 2004-172669 or WO 2004 / 074492); line JOPLIN1 (wheat, disease resistant, not deposited, recorded in US-A 2008-064032); line LL27 (soybean, herbicide tolerant, deposited as NCIMB 41658, described in WO 2006 / 108674 or US-A 2008-320616); line LL55 (soybean, herbicide tolerant, deposited as NCIMB 41660, described in WO 2006 / 108675 or US-A 2008-196127); line LLcotton25 (cotton, herbicide tolerant, deposited as ATCC PTA-3343, described in WO 2003 / 013224 or US A 2003-097687); line LLRICE06 (rice,herbicide tolerance, deposited as ATCC 203353, described in US 6,468,747 or WO2000 / 026345); line LLRice62 (rice, herbicide tolerance, deposited as ATCC 203352, described in WO2000 / 026345), line LLRICE601 (rice, herbicide tolerance, deposited as ATCC PTA-2600, described in US-A2008-2289060 or WO2000 / 026356); line LY038 (maize, quality traits, deposited as ATCC PTA-5623, described in US-A 2007-028322 or WO2005 / 061720); line MIR162 (maize, insect control, deposited as PTA-8166, described in US-A 2009-300784 or WO2007 / 142840); line MIR604 (corn, insect control, not deposited, described in US-A 2008-167456 or WO2005 / 103301); line MON15985 (cotton, insect control, deposited as ATCC PTA-2516, described in US-A 2004-250317 or WO2002 / 100163); line MON810 (corn, insect control, not deposited, described in US-A 2002-102582); line MON863 (corn, insect control, deposited as ATCC PTA-2605, described in WO2004 / 011601 or US-A 2006-095986); line MON87427 (maize, pollination control, deposited as ATCC PTA-7899, described in WO2011 / 062904); line MON87460 (maize, stress resistance, deposited as ATCC PTA-8910, described in WO2009 / 111263 or US-A2011-0138504); line MON87701 (soybean, insect control, deposited as ATCC PTA-8194, described in US-A 2009-130071 or WO2009 / 064652); line MON87705 (soybean, quality trait - herbicide tolerance, deposited as ATCC PTA-9241 deposited, described in US-A2010-0080887 or WO2010 / 037016); line MON87708 (soybean, herbicide tolerance, deposited as ATCC PTA-9670, described in WO2011 / 034704); line MON87712 (soybean, yield, deposited as PTA-10296, described in WO2012 / 051199), line MON87754 (soybean, quality traits, deposited as ATCC PTA-9385,2008-028482 or WO2005 / 059103); line MON88913 (cotton, herbicide tolerance, deposited as ATCC PTA-4854, described in WO2004 / 072235 or US-A 2006-059590); line MON88302 (rapeseed, herbicide tolerant, deposited as PTA-10955, described in WO2011 / 153186), line MON88701 (cotton, herbicide tolerant, deposited as PTA-11754, described in WO2012 / 134808), line MON89034 (corn, insect control, deposited as ATCC PTA-7455, described in WO 07 / 140256 or US-A 2008-260932); line MON89788 (soybean, herbicide tolerant, deposited as ATCC PTA-6708, described in US-A 2006-282915 or WO2006 / 130436); line MS1 1 (canola, pollination control-herbicide tolerance, deposited as ATCC PTA-850 or PTA-2485, described in WO2001 / 031042); line MS8 (canola, pollination control-herbicide tolerance, deposited as ATCC PTA-730, described in WO2001 / 041558 or US-A 2003-188347); line NK603 (maize, herbicide tolerance, deposited as ATCC PTA-2478, described in US-A 2007-292854); line PE-7 (rice, insect control, not deposited, described in WO2008 / 114282); line RF3 (canola, pollination control-herbicide tolerance, deposited as ATCC PTA-730, described in WO2001 / 041558 or US-A 2003-188347); line RT73 (rapeseed, herbicide tolerant, not deposited, described in WO2002 / 036831 or US-A 2008-070260); line SYHT0H2 / SYN-000H2-5 (soybean, herbicide tolerant, deposited as PTA-11226, described in WO2012 / 082548), line T227-1 (sugar beet, herbicide tolerant, not deposited, described in WO2002 / 44407 or US-A 2009-265817); line T25 (maize, herbicide tolerant,not deposited, described in US-A 2001-029014 or WO2001 / 051654); line T304-40 (cotton, insect control-herbicide tolerance, deposited as ATCC PTA-8171, described in US-A 2010-077501 or WO2008 / 122406); line T342-142 (cotton, insect control, not deposited, described in WO2006 / 128568); line TC1507 (maize, insect control-herbicide tolerance, not deposited, described in US-A 2005-039226 or WO2004 / 099447); line VIP1034 (maize, insect control-herbicide tolerance, deposited as ATCC PTA-3925 deposited and described in WO2003 / 052073), Line 32316 (maize, insect control-herbicide tolerance, deposited as PTA-11507 and described in WO2011 / 084632), Line 4114 (maize, insect control-herbicide tolerance, deposited as PTA-11506 and described in WO2011 / 084621), optionally with Line EE-GM1 / LL27 or Line EE-GM2 / LL55 (WO2011 / 063413 A2) stacked line EE-GM3 / FG72 (soybean, herbicide tolerance, ATCC Accession No. PTA-11041), line DAS-68416-4 (soybean, herbicide tolerance, ATCC Accession No. PTA-10442, WO2011 / 066360A1), line DAS-68416-4 (soybean, herbicide tolerance, ATCC Accession No. PTA-10442, WO2011 / 066384A1), line DP-040416-8 (corn, insect control, ATCC Accession No. PTA-11041). ATCC Accession No. PTA-11508, WO2011 / 075593A1), line DP-043A47-3 (corn, insect control, ATCC Accession No. PTA-11509, WO2011 / 075595A1), line DP-004114-3 (corn, insect control, ATCC Accession No. PTA-11506, WO2011 / 084621A1), line DP-032316-8 (corn, insect control, ATCC Accession No. PTA-11507, WO 2011 / 084632A1), line MON-88302-9 (rapeseed, herbicide tolerance, ATCC accession number PTA-10955, WO2011 / 153186A1), line DAS-21606-3 (soybean, herbicide tolerance, ATCC accession number PTA-11028, WO2012 / 033794A2), line MON-87712-4 (soybean, quality traits, ATCC accession number PTA-10296, WO2012 / 051199A2),Strain DAS-44406-6 (soybean, stacked herbicide tolerance, ATCC Accession No. PTA-11336, WO2012 / 075426A1), Strain DAS-14536-7 (soybean, stacked herbicide tolerance, ATCC Accession No. PTA-11335, WO2012 / 075429A1), Strain SYN-000H2-5 (soybean, herbicide tolerance, ATCC Accession No. PTA-1122 6, WO2012 / 082548A2), line DP-061061-7 (rapeseed, herbicide tolerance, no available deposit number, WO2012071039A1), line DP-073496-4 (rapeseed, herbicide tolerance, no available deposit number, US2012131692), line 8264.44.06.1 (soybean, stacked herbicide tolerance, registration number PTA-11336, WO20120754 26A2), line 8291.45.36.2 (soybean, stacked herbicide tolerance, registration number PTA-11335, WO2012075429A2), line SYHT0H2 (soybean, ATCC registration number PTA-11226, WO2012 / 082548A2), line MON88701 (cotton, ATCC registration number PTA-11754, WO2012 / 134808A1), line The strains are KK179-2 (alfalfa, ATCC registration number PTA-11833, WO2013 / 003558A1), pDAB8264.42.32.1 (soybean, stacked herbicide tolerance, ATCC registration number PTA-11993, WO2013 / 010094A1), and MZDT09Y (corn, ATCC registration number PTA-13025, WO2013 / 012775A1).

[0093] In addition, the United States Department of Agriculture (USDA) Animal and Plant Health Inspection Service (APHIS) provides a list of such transgenic strains, which can be found on the Internet at their website aphis.usda.gov Found. For the purposes of this application, this list is relevant as of the filing date of this application.

[0094] The genes / lines which confer the desired traits may also be present in combination with one another in the transgenic plants. Examples of transgenic plants which may be mentioned are important crop plants such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peas and other types of vegetables, cotton, tobacco, rapeseed and fruit plants (including apples, pears, citrus fruits and grapes), with particular emphasis on corn, soybeans, wheat, rice, potatoes, cotton, sugar cane, tobacco and rapeseed. Traits which are particularly emphasized are increased resistance of the plants to insects, arachnids, nematodes and slugs and snails, and increased resistance of the plants to one or more herbicides.

[0095] Commercially available examples of such plants, plant parts or plant seeds which may be preferentially treated according to the invention include ROUNDUP VT VT TRIPLE BOLLGARD ROUNDUP READY 2 ROUNDUP 2XTENDTM、INTACTA RR2 VISTIVE and / or XTENDFLEX TM A commercially available product, such as plant seeds, sold or distributed under a trade name.

[0096] Pathogens

[0097] Polymorph B of the compound of formula (I) can be preferably used as a fungicide. The above diseases include:

[0098] Diseases caused by powdery mildew pathogens, such as Blumeria species, such as Blumeria graminis; Leveillula species, such as Leveillula Taurica; Podosphaera species, such as Podosphaera leucotricha or Podosphaera xanthii; Sphaerotheca species, such as Sphaerotheca fuliginea; Erysiphe species, such as Erysiphe betae and Erysiphe necator;

[0099] Diseases caused by rust pathogens, such as Gymnosporangium species, such as Gymnosporangium sabinae; Hemileia species, such as Hemileia vastatrix; Phakopsora species, such as Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, such as Puccinia recondita, Puccinia graminis or Puccinia striiformis; Uromyces species, such as Uromyces appendiculatus;

[0100] Leaf spot and leaf wilt diseases caused by pathogens such as Alternaria species, such as Alternaria solani or Alternaria mali or Alternaria alternata; Cercospora species, such as Cercosporabeticola; Cladiosporum species, such as Cladiosporium cucumerinum; Cochliobolus species, such as Cochliobolus sativus (conidial form: Drechslera, synonym: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, such as Colletotrichum spp. lindemuthanium or Colletotrichum capsica or Colletotrichum acutatum; Cordana species, for example Cordanamusae; Corynespora species, for example Corynespora cassiicola; Cycloconium species, for example Cycloconium oleaginum; Diaporthe species, for example Diaporthe citri; Elsinoe species, for example Elsinoe fawcettii; Gloeosporium species, for example Gloeosporium oleaginum. laeticolor; Glomerella species, such as Glomerella cingulata; Guignardia species, such as Guignardia bidwelli; Leptosphaeria species, such as Leptosphaeria maculans; Magnaporthe species, such as Magnaporthe grisea;Species of the genus Marsonina, such as Marsonina mali; Species of the genus Microdochium, such as Microdochium nivale; Species of the genus Mycosphaerella, such as Mycosphaerella graminicola, Mycosphaerella arachidicola, and Mycosphaerella fijiensis; Species of the genus Phaeosphaeria, such as Phaeosphaeria nodorum; Species of the genus Pyrenophora, such as Pyrenophora teres, Pyrenophora tritici repentis; Species of the genus Ramularia, such as Ramularia singa. collo-cygni or Ramulariaareola; Rhynchosporium species, such as Rhynchosporium secalis; Septoria species, such as Septoria apii and Septorialycopersii; Setosphaeria species, such as Setosphaeriaturcica; Sclerotinia species, such as Sclerotinia sclerotiorum; Stagonospora species, such as Stagonospora nodorum; Stemphylium species, such as Stemphylium vesicarium; Typhula species, such as Typhula incarnata); Venturia species, such as Venturia inaequalis;

[0101] Root and stem diseases caused by pathogens such as Corticium species, for example Corticium graminearum; Fusarium species, for example Fusarium oxysporum; Gaeumannomyces species, for example Gaeumannomyces graminis; Marsonina species, for example Marsonina mali; Rhizoctonia species, for example Rhizoctonia solani; Sarocladium species, for example Sarocladium oryzae; Sclerotium species, for example Sclerotium oryzae; Tapesia species, for example Tapesia acuformis; species of the genus Thielaviopsis, for example Thielaviopsis basicola;

[0102] Diseases of spadix or panicles (including cobs) caused by pathogens such as Alternaria spp., for example Alternaria spp.; Aspergillus spp., for example Aspergillus flavus; Cladosporium spp., for example Cladosporium cladosporioides; Claviceps spp., for example Claviceps purpurea; Fusarium spp., for example Fusarium culmorum; Gibberella spp., for example Gibberella zeae; Monographella spp., for example Monographella nivalis; Stagnospora spp., for example Stagnosporanodorum;

[0103] Diseases caused by smut fungi, such as: species of the genus Sphacelotheca, such as Sphacelotheca reiliana; species of the genus Tilletia, such as Tilletia caries or Tilletia controversa; species of the genus Urocystis, such as Urocystis occulta; species of the genus Ustilago, such as Ustilago nuda;

[0104] Fruit rot caused by pathogens such as Aspergillus species, such as Aspergillus flavus; Botrytis species, such as Botrytis cinerea; Monilinia species, such as Monilinia laxa; Penicillium species, such as Penicillium expansum or Penicillium purpurogenum; Phomopsis species, such as Phomopsis viticola; Rhizopus species, such as Rhizopus stolonifer; Sclerotinia species, such as Sclerotinia sclerotinia; sclerotiorum); species of the genus Verticilium, for example, Verticilium alboatrum;

[0105] Seed-borne and soil-borne rot and wilt diseases, and seedling diseases caused by pathogens such as Alternaria species, for example Alternaria brassicicola; Aphanomyces species, for example Aphanomyces euteiches; Ascochyta species, for example Ascochyta lentis; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium herbarum; Cochliobolus species, for example Cochliobolus graminis. sativus) (conidial form: Drechslera, Bipolaris synonym: Helminthosporium); Colletotrichum species, for example Colletotrichum coccodes; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Macrophomina species, for example Macrophomina phaseolina; Microdochium species, for example Microdochium nivale; Monographella species, for example Monographella nivalis; Penicillium species, such as Penicillium expansum; Phoma species, such as Phoma lingam; Phomopsis species, such as Phomopsis sojae; Pyrenophora species, such as Pyrenophora graminea; Pyricularia species, such as Pyricularia oryzae; Rhizoctonia species, such as Rhizoctonia solani; Rhizopus species, such as Rhizopus oryzae;Sclerotium species, such as Sclerotium rolfsii; Septoria species, such as Septoria nodorum; Typhula species, such as Typhula incarnata; Verticillium species, such as Verticillium dahliae;

[0106] Cancerous diseases, galls and broom diseases caused by pathogens such as species of the genus Nectria, for example Nectria galligena;

[0107] Wilt diseases caused by pathogens such as Verticillium species, such as Verticillium longisporum; Fusarium species, such as Fusarium oxysporum;

[0108] Deformities of leaves, flowers and fruits caused by pathogens such as Exobasidium species, such as Exobasidium vexans; Taphrina species, such as Taphrina deformans;

[0109] Degenerative diseases of woody plants caused by pathogens such as species of the genus Esca, such as Phaemoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea; such as species of the genus Ganoderma, such as Ganoderma boninense;

[0110] Diseases of plant tubers caused by pathogens such as Rhizoctonia species, for example Rhizoctonia solani; Helminthosporium species, for example Helminthosporium solani;

[0111] Soybean diseases:

[0112] Fungal diseases of leaves, stems, pods and seeds caused by pathogens such as Alternaria leaf spot (Alternaria spec. atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (synonym)), Dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), Leptosphaerulina leaf spot (Leptosphaerulina trifolii), Leveillula powdery mildew (Leveillula Taurica), Phyllostica leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), Pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage and web blight (Rhizoctonia solani), solani), rust (Phakopsora pachyrhizi), Phakopsorameibomiae), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), sudden death syndrome (Fusarium virguliforme), target spot (Corynespora cassiicola);

[0113] Fungal diseases of roots and stems caused by pathogens such as black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), Fusarium wilt or wilt, root rot and pod and crown rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti, mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmopspora vasinfecta), pod and stem wilt (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), brown stem rot (Phialophora gregata), Rhizoctonia root rot, stem rot and damping-off (Rhizoctonia solani), Sclerotinia stem rot (Sclerotinia sclerotiorum), Sclerotinia white rot (Sclerotiniarolfsii), Thielaviopsis root rot (Thielaviopsis basicola).

[0114] Preferably, the present invention relates to the use of polymorph B of the compound of formula (I) for controlling the following diseases: diseases caused by powdery mildew pathogens, such as Blumeria species, such as Blumeria graminis of the Poaceae family; Leveillula species, such as Leveillula Taurica; Podosphaera species, such as Podosphaeraleucotricha or Podosphaera xanthii; Sphaerotheca species, such as Sphaerotheca fuliginea; Erysiphe species, such as Erysiphe betae and Erysiphe necator;

[0115] Diseases caused by rust pathogens, such as Gymnosporangium species, such as Gymnosporangium sabinae; Hemileia species, such as Hemileia vastatrix; Phakopsora species, such as Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, such as Puccinia recondita, Puccinia graminis or Puccinia striiformis; Uromyces species, such as Uromyces appendiculatus;

[0116] Leaf spot and leaf wilt diseases caused by pathogens such as Alternaria species, such as Alternaria solani or Alternaria mali or Alternaria alternata; Cercospora species, such as Cercosporabeticola; Cladiosporum species, such as Cladiosporium cucumerinum; Cochliobolus species, such as Cochliobolus sativus (conidial form: Drechslera, synonym: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, such as Colletotrichum spp. lindemuthanium or Colletotrichum capsica or Colletotrichum acutatum; Corynespora species, for example Corynespora cassiicola; Cycloconium species, for example Cycloconium oleaginum; Diaporthe species, for example Diaporthecitri; Elsinoe species, for example Elsinoe fawcettii; Erysiphe species, such as Erysiphe betae and Erysiphe necator; Gloeosporium species, for example Gloeosporium oleaginum; laeticolor; Glomerella species, such as Glomerella cingulata; Guignardia species, such as Guignardia bidwelli; Leptosphaeria species, such as Leptosphaeria maculans; Magnaporthe species, such as Magnaporthe grisea;Species of the genus Marsonina, such as Marsoninamali; Species of the genus Microdochium, such as Microdochium nivale; Species of the genus Mycosphaerella, such as Mycosphaerella graminicola, Mycosphaerella arachidicola, and Mycosphaerella fijiensis; Species of the genus Phaeosphaeria, such as Phaeosphaeria nodorum; Species of the genus Phyllachora, such as Phyllachora maydis; Species of the genus Pyrenophora, such as Pyrenophora teres, Pyrenophora tritici repentis; Ramularia species, such as Ramularia collo-cygni or Ramularia areola; Rhynchosporium species, such as Rhynchosporium secalis; Septoria species, such as Septoria apii and Septoria lycopersii; Setosphaeria species, such as Setosphaeria turcica; Sclerotinia species, such as Sclerotiniasclerotiorum; Stagonospora species, such as Stagonospora anodorum; Stemphylium species, such as Stemphylium swellii. vesicarium; species of the genus Typhula, such as Typhula incarnata; species of the genus Venturia, such as Venturia inaequalis;

[0117] Root and stem diseases caused by pathogens such as Corticium species, for example Corticium graminearum; Fusarium species, for example Fusarium oxysporum; Gaeumannomyces species, for example Gaeumannomyces graminis; Marsonina species, for example Marsonina mali; Rhizoctonia species, for example Rhizoctonia solani; Sarocladium species, for example Sarocladium oryzae; Sclerotium species, for example Sclerotium oryzae; Tapesia species, for example Tapesia acuformis; species of the genus Thielaviopsis, for example Thielaviopsis basicola;

[0118] Diseases of spadix or panicles (including cobs) caused by pathogens such as Alternaria spp., for example Alternaria spp.; Aspergillus spp., for example Aspergillus flavus; Cladosporium spp., for example Cladosporium cladosporioides; Claviceps spp., for example Claviceps purpurea; Fusarium spp., for example Fusarium culmorum; Gibberella spp., for example Gibberella zeae; Monographella spp., for example Monographella nivalis; Stagnospora spp., for example Stagnosporanodorum;

[0119] Diseases caused by smut fungi, such as: species of the genus Sphacelotheca, such as Sphacelotheca reiliana; species of the genus Tilletia, such as Tilletia caries or Tilletia controversa; species of the genus Urocystis, such as Urocystis occulta; species of the genus Ustilago, such as Ustilago nuda;

[0120] Fruit rot caused by pathogens such as Aspergillus species, such as Aspergillus flavus; Botrytis species, such as Botrytis cinerea; Monilinia species, such as Monilinia laxa; Penicillium species, such as Penicillium expansum or Penicillium purpurogenum; Phomopsis species, such as Phomopsis viticola; Rhizopus species, such as Rhizopus stolonifer; Sclerotinia species, such as Sclerotinia sclerotinia; sclerotiorum); species of the genus Verticilium, for example, Verticilium alboatrum;

[0121] Seed-borne and soil-borne rot and wilt diseases, and seedling diseases caused by pathogens such as Alternaria species, for example Alternaria brassicicola; Aphanomyces species, for example Aphanomyces euteiches; Ascochyta species, for example Ascochyta lentis; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium herbarum; Cochliobolus species, for example Cochliobolus graminis. sativus) (conidial form: Drechslera, Bipolaris synonym: Helminthosporium); Colletotrichum species, for example Colletotrichum coccodes; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Macrophomina species, for example Macrophomina phaseolina; Microdochium species, for example Microdochium nivale; Monographella species, for example Monographella nivalis; Penicillium species, such as Penicillium expansum; Phoma species, such as Phoma lingam; Phomopsis species, such as Phomopsis sojae; Pyrenophora species, such as Pyrenophora graminea; Pyricularia species, such as Pyricularia oryzae; Rhizoctonia species, such as Rhizoctonia solani;Rhizopus species, such as Rhizopus oryzae; Sclerotium species, such as Sclerotium rolfsii; Septoria species, such as Septoria nodorum; Typhula species, such as Typhula incarnata; Verticillium species, such as Verticillium dahliae;

[0122] Cancerous diseases, galls and broom diseases caused by pathogens such as species of the genus Nectria, for example Nectria galligena;

[0123] Wilt diseases caused by pathogens such as Verticillium species, such as Verticillium longisporum; Fusarium species, such as Fusarium oxysporum;

[0124] Deformities of leaves, flowers and fruits caused by pathogens such as Exobasidium species, such as Exobasidium vexans; Taphrina species, such as Taphrina deformans;

[0125] Degenerative diseases of woody plants caused by pathogens such as species of the genus Esca, such as Phaemoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea; such as species of the genus Ganoderma, such as Ganoderma boninense;

[0126] Diseases of plant tubers caused by pathogens such as Rhizoctonia species, for example Rhizoctonia solani; Helminthosporium species, for example Helminthosporium solani;

[0127] Soybean diseases:

[0128] Fungal diseases of leaves, stems, pods and seeds caused by pathogens such as Alternaria leaf spot (Alternaria spec. atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (synonym)), Dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), Leptosphaerulina leaf spot (Leptosphaerulina trifolii), Leveillula powdery mildew (Leveillula Taurica), Phyllostica leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), Pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage and web blight (Rhizoctonia solani), solani), rust (Phakopsora pachyrhizi), Phakopsorameibomiae), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), sudden death syndrome (Fusarium virguliforme), target spot (Corynespora cassiicola);

[0129] Fungal diseases of roots and stems caused by pathogens such as black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), Fusarium wilt or wilt, root rot and pod and crown rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti, mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmopspora vasinfecta), pod and stem wilt (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), brown stem rot (Phialophora gregata), Rhizoctonia root rot, stem rot and damping-off (Rhizoctonia solani), Sclerotinia stem rot (Sclerotinia sclerotiorum), Sclerotinia white rot (Sclerotiniarolfsii), Thielaviopsis root rot (Thielaviopsis basicola).

[0130] More preferably, the present invention relates to the use of polymorph B of the compound of formula (I) for controlling the following diseases: diseases caused by powdery mildew pathogens, such as Blumeria species, such as Blumeria graminis of the Poaceae family; Leveillula species, such as Leveillula Taurica; Podosphaera species, such as Podosphaeraleucotricha or Podosphaera xanthii; Sphaerotheca species, such as Sphaerotheca fuliginea; Uncinula species, such as Uncinula necator;

[0131] Leaf spot and leaf wilt diseases caused by pathogens such as Alternaria species, such as Alternaria solani or Alternaria mali or Alternaria alternata; Cercospora species, such as Cercosporabeticola; Cladiosporum species, such as Cladiosporium cucumerinum; Cochliobolus species, such as Cochliobolus sativus (conidial form: Drechslera, synonym: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, such as Colletotrichum spp. lindemuthanium or Colletotrichum capsica or Colletotrichum acutatum; Corynespora species, for example Corynespora cassiicola; Cycloconium species, for example Cycloconium oleaginum; Diaporthe species, for example Diaporthecitri; Elsinoe species, for example Elsinoe fawcettii; Erysiphe species, such as Erysiphe betae and Erysiphe necator; Gloeosporium species, for example Gloeosporium oleaginum; laeticolor; Glomerella species, such as Glomerella cingulata; Guignardia species, such as Guignardia bidwelli; Leptosphaeria species, such as Leptosphaeria maculans; Magnaporthe species, such as Magnaporthe grisea;Species of the genus Marsonina, such as Marsoninamali; Species of the genus Microdochium, such as Microdochium nivale; Species of the genus Mycosphaerella, such as Mycosphaerella graminicola, Mycosphaerella arachidicola, and Mycosphaerella fijiensis; Species of the genus Phaeosphaeria, such as Phaeosphaeria nodorum; Species of the genus Pyrenophora, such as Pyrenophora teres, Pyrenophoratritici repentis; Species of the genus Ramularia, such as Ramularia singa. collo-cygni or Ramularia areola; Rhynchosporium species, such as Rhynchosporium secalis; Septoria species, such as Septoria apii and Septoria lycopersii; Setosphaeria species, such as Setosphaeria turcica; Sclerotinia species, such as Sclerotiniasclerotiorum; Stagonospora species, such as Stagonosporanodorum; Stemphylium species, such as Stemphylium vesicarium; Typhula species, such as Typhula incarnata); Venturia species, such as Venturia inaequalis;

[0132] Root and stem diseases caused by pathogens such as Corticium species, for example Corticium graminearum; Fusarium species, for example Fusarium oxysporum; Gaeumannomyces species, for example Gaeumannomyces graminis; Marsonina species, for example Marsonina mali; Rhizoctonia species, for example Rhizoctonia solani; Sarocladium species, for example Sarocladium oryzae; Sclerotium species, for example Sclerotium oryzae; Tapesia species, for example Tapesia acuformis; species of the genus Thielaviopsis, for example Thielaviopsis basicola;

[0133] Diseases of spadix or panicles (including cobs) caused by pathogens such as Alternaria spp., for example Alternaria spp.; Aspergillus spp., for example Aspergillus flavus; Cladosporium spp., for example Cladosporium cladosporioides; Claviceps spp., for example Claviceps purpurea; Fusarium spp., for example Fusarium culmorum; Gibberella spp., for example Gibberella zeae; Monographella spp., for example Monographella nivalis; Stagnospora spp., for example Stagnosporanodorum;

[0134] Fruit rot caused by pathogens such as Aspergillus species, such as Aspergillus flavus; Botrytis species, such as Botrytis cinerea; Monilinia species, such as Monilinia laxa; Penicillium species, such as Penicillium expansum or Penicillium purpurogenum; Phomopsis species, such as Phomopsis viticola; Rhizopus species, such as Rhizopus stolonifer; Sclerotinia species, such as Sclerotinia sclerotinia; sclerotiorum); species of the genus Verticilium, for example, Verticilium alboatrum;

[0135] Seed-borne and soil-borne rot and wilt diseases, and seedling diseases caused by pathogens such as Alternaria species, for example Alternaria brassicicola; Aphanomyces species, for example Aphanomyces euteiches; Ascochyta species, for example Ascochyta lentis; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium herbarum; Cochliobolus species, for example Cochliobolus graminis. sativus) (conidial form: Drechslera, Bipolaris synonym: Helminthosporium); Colletotrichum species, for example Colletotrichum coccodes; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Macrophomina species, for example Macrophomina phaseolina; Microdochium species, for example Microdochium nivale; Monographella species, for example Monographella nivalis; Penicillium species, such as Penicillium expansum; Phoma species, such as Phoma lingam; Phomopsis species, such as Phomopsis sojae; Pyrenophora species, such as Pyrenophora graminea; Pyricularia species, such as Pyricularia oryzae; Rhizoctonia species, such as Rhizoctonia solani;Rhizopus species, such as Rhizopus oryzae; Sclerotium species, such as Sclerotium rolfsii; Septoria species, such as Septoria nodorum; Typhula species, such as Typhula incarnata; Verticillium species, such as Verticillium dahliae;

[0136] Fusarium species, for example Fusarium oxysporum;

[0137] Soybean diseases:

[0138] Fungal diseases of leaves, stems, pods and seeds caused by pathogens such as Alternaria leaf spot (Alternaria spec. atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var.truncatum), brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (synonym)), Dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), Leptosphaerulina leaf spot (Leptosphaerulina trifolii), powdery mildew (Leveillula powdery mildew (Leveillula Taurica), Phyllostica leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), Pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage and web blight (Rhizoctonia solani), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), sudden death syndrome (Fusarium virguliforme), target spot (Corynespora cassiicola);.

[0139] Fungal diseases of roots and stems caused by pathogens such as black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), Fusarium wilt or wilt, root rot and pod and crown rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti, mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmopspora vasinfecta), pod and stem wilt (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), brown stem rot (Phialophora gregata), Rhizoctonia root rot, stem rot and damping-off (Rhizoctonia solani), Sclerotinia stem rot (Sclerotinia sclerotiorum), Sclerotinia white rot (Sclerotiniarolfsii), Thielaviopsis root rot (Thielaviopsis basicola).

[0140] Most preferably, the present invention relates to the use of polymorph B of the compound of formula (I) for controlling the following diseases: diseases caused by powdery mildew pathogens, the pathogens being species of the genus Sphaerotheca, such as Sphaerotheca fuliginea;

[0141] Leaf spot and leaf wilt diseases caused by pathogens such as Alternaria species, such as Alternaria solani or Alternaria mali or Alternaria alternata; Cercospora species, such as Cercosporabeticola; Colletotrichum species, such as Colletotrichum lindemuthanium or Colletotrichum capsica or Colletotrichum acutatum; Diaporthe species, such as Diaporthe citri; Phaeosphaeria species, such as Phaeosphaeria glumenosum. nodorum; species of the genus Pyrenophora, such as Pyrenophora teres and Pyrenophora tritici repentis; species of the genus Septoria, such as Septoria apii and Septoria lycopersii;

[0142] Root and stem diseases caused by pathogens such as Fusarium species, for example Fusarium oxysporum;

[0143] Diseases of spadix or panicles (including cobs) caused by pathogens such as Alternaria species, for example Alternaria spp.; Fusarium species, for example Fusarium culmorum;

[0144] Botrytis species, for example Botrytis cinerea; seed-borne and soil-borne rot and wilt diseases, and seedling diseases caused by, for example, Alternaria species, for example Alternaria brassicicola; Colletotrichum species, for example Colletotrichum coccodes; Fusarium species, for example Fusarium culmorum; Pyrenophora species, for example Pyrenophora graminea; Pyricularia species, for example Pyricularia oryzae;

[0145] Fusarium species, for example Fusarium oxysporum.

[0146] Mycotoxins

[0147] In addition, polymorph B of the compound of formula (I) and compositions comprising the same can reduce the content of mycotoxins in harvested materials and foods and feeds prepared therefrom. In particular, mycotoxins include, but are not limited to, the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2-toxin and HT2-toxin, fumonisin, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroprolifer in), fusarenol, ochratoxins, patulin, ergotalkaloids and aflatoxin, which toxins can be produced, for example, by the following fungi: Fusarium species, such as F. acuminatum, F. asiaticum, F. avenaceum, F. crookwellense, F. culmorum, F. graminearum (Gibberella zeae), F.equiseti, F.fujikoroi, F.musarum, F.oxysporum, F.proliferatum, F.poae, F.pseudograminearum, F.sambucinum, F.scirpi, F.semitectum, F.solani, F.sporogonum, F.ssporium porotrichoides), F. langsethiae, F. subglutinans, F. tricinctum, F. verticillioides, etc.; and Aspergillus species, such as A. flavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, A.versicolor; Penicillium species, such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti; Claviceps species, such as C. purpurea, C. fusiformis, C. paspali, C. africana; Stachybotrys species and others. .

[0148] Material protection

[0149] Polymorph B of the compound of formula (I) and compositions comprising it can also be used in the protection of materials, in particular for protecting industrial materials from attack and destruction by phytopathogenic fungi.

[0150] Furthermore, polymorph B of the compound of formula (I) and compositions comprising the same can be used as antifouling compositions alone or in combination with other active ingredients.

[0151] In this article, Industrial Materials Should be understood to mean the inanimate material prepared for industrial application.For example, the industrial material that can be protected from microbial alteration or destruction can be adhesive, glue, paper, wallpaper and wood board / cardboard, textile, carpet, leather, timber, fiber and tulle, paint and plastic products, cooling lubricant and other materials that can be infected or destroyed by microorganisms. The parts (for example cooling water loop, cooling and heating system and ventilation and air conditioning unit) of the production equipment and building that can be damaged by the proliferation of microorganisms are also included in the scope of material to be protected.Within the scope of the present invention, industrial material preferably comprises adhesive, size, paper and card, leather, timber, paint, cooling lubricant and heat transfer fluid, more preferably timber.

[0152] Polymorph B of the compound of formula (I) and compositions comprising the same can prevent various adverse effects, such as decay, spoilage, discoloration, fading or mold.

[0153] In the case of treating wood, polymorph B of the compound of formula (I) and compositions comprising the same can also be used to combat fungal diseases susceptible to growth on or in the wood surface.

[0154] woodIt means all types of wood species and all types of processed products of this wood used for construction, such as solid wood, high-density wood, laminated wood and plywood. In addition, polymorph B of the compound of formula (I) and compositions comprising it can be used to protect objects that come into contact with salt water or brackish water from contamination, in particular hulls, screens, nets, buildings, moorings and signal systems.

[0155] The polymorphic form B of the compound of formula (I) and the composition comprising it can also be used to protect storage. Storage should be understood to mean natural substances or processed products of plant origin or animal origin, which are of natural origin and need long-term protection. Storage of plant origin such as plants or plant parts (such as stems, leaves, tubers, seeds, fruits, grains) can be protected just after harvesting or by (pre) drying, moistening, crushing, grinding, squeezing or baking processing. Storage also includes wood, including unprocessed wood (such as building wood, electric poles and fences) or wood (such as furniture) in finished product form. Storage of animal origin is such as hides, leather, fur and hair. The polymorphic form B of the compound of formula (I) and the composition comprising it can prevent a variety of adverse effects, such as rotting, decaying, discoloring, fading or mildew.

[0156] Microorganisms capable of degrading or modifying industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms. Polymorph B of the compound of formula (I) and compositions comprising it preferably act on fungi, in particular molds, wood-discoloring and wood-destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), as well as on slime organisms and algae.Examples include microorganisms of the genera Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophorapuetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, for example, Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp., Poria spp., Serpula spp., and Tyromyces spp., Cladosporium spp., Paecilomyces spp., Mucor spp., Escherichia, for example, Escherichia coli; Pseudomonas, for example, Pseudomonas aeruginosa. aeruginosa); Staphylococcus, for example Staphylococcus aureus, Candida and Saccharomyces spp., for example Saccharomyces cerevisae. The plant protection agents may additionally comprise one or more other active ingredients, such as fungicides, bactericides, acaricides, nematicides, insecticides, biological control agents or herbicides.Mixtures with fertilizers, growth regulators, safeners, nitrification inhibitors, semichemicals and / or other agriculturally beneficial preparations are also possible. This can broaden the activity spectrum or prevent the development of resistance.

[0157] In another embodiment, the present invention also relates to a plant protection agent comprising polymorph B of a compound of formula (I) which further comprises one or more other active substances selected from the group consisting of fungicides, insecticides, herbicides, acaricides, safeners and / or plant growth regulators.

[0158] The active compounds described herein by their common names are known and described, for example, in “The Pesticide Manual” (“The Pesticide Manual” 17th edition, British Crop Protection Council 2015) or can be found on the Internet (eg http: / / www.alanwood.net / pesticides).

[0159] Examples of fungicides that can be mixed with the compounds and compositions of the present invention are:

[0160] 1) Inhibitors of ergosterol biosynthesis, such as (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenbuconazole, (1.005) fenhexamid, (1.006) fenpropidin, (1.007) fenpropimorph, ropimorph), (1.008) fenpyrazamine, (1.009) fluoxytioconazole, (1.010) fluquinconazole, (1.011) flutriafol, (1.012) hexaconazole, (1.013) imazalil, (1.014) imazalil sulfate sulfate), (1.015) ipconazole, (1.016) ipfentrifluconazole, (1.017) mefentrifluconazole, (1.018) metconazole, (1.019) myclobutanil, (1.020) paclobutrazol, (1.021) penconazole, (1.022) prochloraz, (1.023) propiconazole, (1.024) prothioconazole, (1.025) pyrisoconazole oxazole), (1.026) spiroxamine, (1.027) tebuconazole, (1.028) tetraconazole, (1.029) triadimenol, (1.030) tridemorph, (1.031) triticonazole, (1.032) (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.033) (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.034)034) (2R) -2- (1-chlorocyclopropyl) -4- [(1R) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.035) (2R) -2- (1-chlorocyclopropyl) -4- [(1S) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.036) (2R) -2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) propan-2-ol, (1.037) (2S) -2- (1-chlorocyclopropyl) -4- [(1R) -2,2-dichlorocyclopropyl] -1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.038) (2S) -2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.039) (2S) -2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.040) (R) -[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.041) (S) -[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, -2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.042) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.043) 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.044) 1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl) -1H-1,2,4-triazole, (1.045) 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.046) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.047) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.048)048) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.049) 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.050) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.051) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.052) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.053) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.054) 2-[(2 S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.055) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.056) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.057) 2-[6-(4-bromophenoxy-2-(trifluoromethyl) -3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.058) 2-[6-(4-chlorophenoxy-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.059) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.060) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.061) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.062) 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, (1.063) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.064) 5-(allylthio)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole-3-thione triazole, (1.065) 5-(allylthio)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.066) 5-(allylthio)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.067) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoic acid methyl ester, (1.068) N'-(2,5-dimethyl-4-(2-methylbenzyl)phenyl)- N-ethyl-N-formamidine methyl ester, (1.069) N'-(2-chloro-4-(4-cyanobenzyl)-5-methyl-phenyl)-N-ethyl-N-cyanobenzyl, (1.070) N'-(2-chloro-4-(4-methoxy-benzyl)-5-methylphenyl)-N-ethyl-N-formamidine methyl ester, (1.071) N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyliminocarboxamide, (1.072) N'-(4-benzyl-2-chloro-5-methylphenyl)-N-ethyl-N-formamidine methyl ester, (1.073) N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyliminocarboxamide, (1.074) N'-[5 -bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methyliminocarboxamide, (1.075) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methyliminocarboxamide, (1.076) N'-{5-bromo-2-methyl-6-[(1-propoxyprop-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.077) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.078) N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.079) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.080) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide Aminoformamide, (1.081) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminoformamide, (1.082) N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl]-N-methyliminoformamide, (1.083) p-Tolylmethyl 4-[(E)-[ethyl(methyl)amino]methyleneamino]-2,5-dimethyl-benzoate.

[0161] 2) Inhibitors of respiratory complex I or II, for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) cyclobutrifluram, (2.006) flubeneteram, (2.007) fluindapyr, (2.008) fluopyram, (2.009) flutolamid, nil), (2.010) fluxapyroxad, (2.011) furametpyr, (2.012) inpyrfluxam, (2.013) isofetamid, (2.014) isoflucypram, (2.015) isopyrazam, (2.016) penflufen, (2.017) penthiopyrad, (2.018) pydiflumetofen, (2.019) pyrapropoy ne, (2.020) Pyraziflumid, (2.021) sedaxane, (2.022) Thifluzamide (also known as trifluzamide), (2.023) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.024) 5-chloro-N-[2-[1-(4-chlorophenyl)pyrazol-3-yl]ethoxy]-6-ethyl-pyrimidin-4-amine, (2.025) N-[2-[1-(4-chlorophenyl)pyrazol-3-yl]ethoxy]quinazolin- 4-amine, (2.026) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.027) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.028) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.029) 1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (2.030) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.031) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.032) 3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2 ,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.033) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.034) 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1-methyl-1H-pyrazole-4-carboxamide, (2.035) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.036) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, Hydrogen-1,4-naphthylene-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N-[1-(2,4-dichlorophenyl)-1-methoxyprop-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.038) N-[rac-(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide. .

[0162] 3) Inhibitors of respiratory complex III, such as (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) oxadiazine famoxadone, (3.010) fenamidone, (3.011) fenpicoxamid, (3.012) florylpicoxamid, (3.013) flufenoxystrobin, (3.014) fluoxastrobin, (3.015) kresoxim-methyl, (3.016) mandestrobin, (3.017) metaylpicoxamid, (3.018) metominostrobin 、(3.019) metyltetraprole、(3.020) orysastrobin、(3.021) picoxystrobin、(3.022) pyraclostrobin、(3.023) pyrametostrobin、(3.024) pyraoxystrobin、(3.025) trifloxystrobin、(3.026) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl] oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.027) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.028) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.030)030) (2S) -2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.031) (Z,2E) -5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethylpent-3-enoamide, (3.032) (Z) -2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester, (3.033) (Z) -2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester, (3.034) (Z) -3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2- 1-methyl-2-enoate, (3.035) (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)methoxy]phenoxy]prop-2-enoate, (3.036) methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate, (3.037) (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoic acid [rac-2-(4-bromo-7-fluoro-indol-1-yl)-1-methyl-propyl] ester, (3.038) (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoic acid [rac-2-(7-bromo-4-fluoro-indol-1-yl)-1-methyl-propyl] ester methyl-propyl] ester, (3.039) (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [rac-2-(7-bromoindol-1-yl)-1-methyl-propyl] ester, (3.040) (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [rac-2-(3,5-dichloro-2-pyridyl)-1-methyl-propyl] ester, (3.041) (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [(1S)-1-[1-(1-naphthyl)cyclopropyl]ethyl] ester, (3.042) (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [rac-2-(7-bromoindol-1-yl)-1-methyl-propyl] ester, (3.043) (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [rac-2-(7-bromoindol-1-yl)-1-methyl-propyl] ester, (3.044) ester, (3.043) (2S)-2-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]propionic acid [(1S)-1-[1-(1-naphthyl)cyclopropyl]ethyl] ester, (3.044) 2-methylpropionic acid [2-[[(1S)-2-[(1RS,2SR)-2-(3,5-dichloro-2-pyridinyl)-1-methyl-propyl]-1-methyl-2-oxo-ethyl]carbamoyl]-4-methoxy-3-pyridinyl]oxymethyl ester, (3.045) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide. .

[0163] 4) Inhibitors of mitosis and cell division, for example (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) fluopimomide, (4.006) metrafenone, (4.007) pencycuron, (4.008) pyridachlometyl, (4.009) pyriofenone (chlazafe none), (4.010) thiabendazole, (4.011) thiophanate-methyl, (4.012) zoxamide, (4.013) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.014) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.016) 4-(2-bromo-4 -fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.017) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.018) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.019) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.020) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.0 21) 4-(2-chloro-4-fluorophenyl)-N-(2,6-dichlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.022) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.023) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.024) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.025) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (4.026)026) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.027) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.028) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine. .

[0164] 5) Compounds capable of multi-site action, such as (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, oxychloride), (5.009) copper sulfate (2+), (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) metiram zinc zinc), (5.017) oxine-copper, (5.018) propineb, (5.019) sulfur and sulfur preparations including calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022) ziram, (5.023) 6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile.

[0165] 6) Compounds that can induce host defense, such as (6.001) acibenzolar-S-methyl, (6.002) fosetyl-aluminum, (6.003) fosetyl-calcium, (6.004) fosetyl-sodium, (6.005) isotianil, (6.006) phosphorous acid and its salts, (6.007) probenazole, and (6.008) tiadinil.

[0166] 7) Inhibitors of amino acid and / or protein biosynthesis, for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil.

[0167] 8) Inhibitors of ATP production, for example (8.001) silthiofam.

[0168] 9) Inhibitors of cell wall synthesis, for example (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.009) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

[0169] 10) Inhibitors of lipid synthesis or transport or membrane synthesis, for example (10.001) fluoxapiprolin, (10.002) natamycin, (10.003) oxathiapiprolin, (10.004) propamocarb, (10.005) propamocarb hydrochloride, hydrochloride), (10.006) propamocarb-fosetylate, (10.007) tolclofos-methyl, (10.008) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (10.009) 1-(4-{4 -[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (10.010) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (10.011) 2-[3, 5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (10.012) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (10.013) 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (10.014) 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (10.015) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulfonate, (10.016) methanesulfonic acid 3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodiazepin-6-yl} ester, (10.017) methanesulfonic acid 9-fluoro-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodiazepin-6-yl} ester, 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (10.019) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-9-fluoro-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate. .

[0170] 11) Inhibitors of melanin biosynthesis, for example (11.001) tolprocarb, (11.002) tricyclazole.

[0171] 12) Inhibitors of nucleic acid synthesis, for example, (12.001) benalaxyl, (12.002) benalaxyl-M, kiralaxyl, (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

[0172] 13) Inhibitors of signal transduction, for example, (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen, (13.006) vinclozolin.

[0173] 14) Compounds that can act as uncouplers, for example (14.001) fluazinam and (14.002) meptyldinocap.

[0174] 15) Other fungicides, such as (15.001) abscisic acid, (15.002) aminopyrifen, (15.003) benthiazole, (15.004) bethoxazin, (15.005) capsimycin, (15.006) carvone, (15.007) chinomethionat, (15.008) chloroinconazide, (15.009) cufraneb, (15.010) cyflufenamid, (15.011) cymoxanil Cymoxanil, (15.012) cyprosulfamide, (15.013) dipymetitrone, (15.014) D-tagatose, (15.015) flufenoxadiazam, (15.016) flumetylsulforim, (15.017) flutianil, (15.018) ipflufenoquin, (15.019) methyl isothiocyanate, (15.020) mildiomycin, (15.021) nickel dimethyldithiocarbamate), (15.022) nitrothal-isopropyl, (15.023) oxyfenthiin, (15.024) pentachlorophenol and its salts, (15.025) picarbutrazox, (15.026) quinofumelin, (15.027) tebufloquin, (15.028) tecloftalam, (15.029) tolnifanide, (15.030) 2-(6-benzylpyridin-2-yl)quinazoline, (15.031) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15.032) 2-phenylphenol and salts, (15.033) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(1H)-one), (15.034) 4-oxo-4-[(2-phenylethyl)amino]butyric acid, (15.035) 5-amino-1,3,4-thiadiazole-2-thiol, (15.036) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonylhydrazide, (15.037) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonylhydrazide, (15.038) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonylhydrazide, (15.039) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonylhydrazide, (15.040) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonylhydrazide, (15.041) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonylhydrazide, (15.042) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonylhydr037) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.038) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.039) but-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.040) (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.041) methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, (15.042) N-acetyl-N-[2-bromo-4-(trifluoromethyl) 1-(4-(6-fluoro-2-methyl-3-quinolyl)-2,4-dimethyl-pentanamide, (15.048) (2S)-2-benzyl-N-(8-fluoro-2-methyl-3-quinolyl)-2,4-dimethyl-pentanamide, (15.049) 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl- 3,4-dihydroisoquinoline, (15.050) 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, (15.051) 1-(5-(fluoromethyl)-6-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.052) 1-(5,6-dimethylpyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.053) 1-(6-(difluoromethyl)-5-methoxy-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.054) 1-(6-(difluoromethyl)-5-methyl -pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.055) 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-3,4-isoquinoline, (15.056) 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.057) 2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.058) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.059) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)-8-fluoroquinoline, (15.060) 3-(4,4-difluoro-5,5-dimethyl-4,5-dihydrothieno[2,3-c]pyridin-7-yl)quinoline, (15.061) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.062) 4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, (15.063) 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, (15.064 )5-bromo-1-(5,6-dimethylpyridin-3-yl)-3,3-dimethyl-3,4-dihydroisoquinoline, (15.065)7,8-difluoro-N-[rac-1-benzyl-1,3-dimethyl-butyl]quinoline-3-carboxamide, (15.066)8-fluoro-3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.067)8-fluoro-3-(5-fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.068)8-fluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)quinoline-3-carboxamide, (15.069)8-fluoro-N -[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, (15.070) 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, (15.071) 8-fluoro-N-[(2S)-4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl]quinoline-3-carboxamide, (15.072) 8-fluoro-N-[rac-1-[(3-8-fluoro-N-[(2S)-4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl]quinoline-3-carboxamide)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide 、(15.073) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine、(15.074) N-(2,4-dimethyl-1-phenylpentan-2-yl)-8-fluoroquinoline-3-carboxamide、(15.075) N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide、(15.076) N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide、(15.077) N-[(2R)-2,4-dimethyl-1-phenylpentan-2-yl)-8-fluoroquinoline-3-carboxamide、(15.078) rac-2-benzyl-N-(8-fluoro-2-methyl-3-quinolyl)-2,4-dimethyl-pentanamide, (15.079) 1,1-diethyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.080) 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.081) 1-[[3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one, (15.082) 1-[[4-[5-(trifluoromethyl)-1, 2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.083) 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.084) 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.085) 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.086) 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropyloxy]pyrimidine 2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.089) 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)oxadiazol-3-yl]phenyl]methyl]urea, (15.090) 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidine-2-one, (15.087) 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide, (15.088) 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.089) 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)oxadiazol-3-yl]phenyl]methyl]urea, -one, (15.091) 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolin-3-one, (15.092) dimethylcarbamic acid 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl ester, (15.093) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolin-3-one, (15.094) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine, (15.095) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-(2,6-difluorophenyl)propyl]pyrimidin-2-amine, (15.096) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-(2-fluorophenyl)ethyl]pyrimidin-2-amine, (15.097) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-(2-fluorophenyl)ethyl]pyrimidin-2-amine, (15.098) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-(3,5-difluorophenyl)ethyl]pyrimidin-2 -amine, (15.099) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-phenylethyl]pyrimidin-2-amine, (15.100) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine, (15.101) 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.102) 1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-pyrazole-4-carboxylic acid ethyl ester, (15.103) {4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-pyrazole-4-carboxylic acid ethyl ester, 1,2,4-oxadiazol-3-yl]phenyl}carbamic acid methyl ester, (15.104) N-(1-methylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.105) N-(2,4-difluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.106) N,2-dimethoxy-N-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, (15.107) N,N-dimethyl-1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-1,2,4-triazole -3-amine, (15.108) N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.109) N-[(E)-N-methoxy-C-methyl-carbonimino]-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.110) N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.111) N-[(Z)-N-methoxy-C-methyl-carbonimino]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.112) N-[[2,3-difluoro-4-[5-(N-[[2,3-)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propionamide, (15.113) N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, (15.114) N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, (15 .115) N-{2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}butanamide, (15.116) N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}cyclopropanecarboxamide, (15.117) N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}propanamide, (15.118) N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}cyclopropanecarboxamide )-1,2,4-oxadiazol-3-yl)phenyl]methyl]acetamide, (15.119) N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, (15.120) N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, (15.121) N-methoxy-N-[[4-[5-(trifluoromethyl) -1,2,4-oxadiazol-3-yl]phenyl]methyl)cyclopropanecarboxamide, (15.122) N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.123) N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide, (15.124) N-methyl-N-phenyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide.

[0175] All named mixing components of the abovementioned classes (1) to (15) may be present in the form of free compounds or, if their functional groups are capable of salt formation, in the form of their agriculturally acceptable active salts.

[0176] The compounds and compositions of the present invention may also be combined with one or more biological control agents.

[0177] As used herein, the term "biological control" is defined as the control of pests, such as phytopathogenic fungi and / or insects and / or mites and / or nematodes, by the use or utilization of biological control agents.

[0178] As used herein, the term "biological control agent" is defined as an organism that is not a pest and / or a protein or secondary metabolite produced by such an organism for biological control purposes. Mutants of a second organism should be included in the definition of biological control agent. The term "mutant" refers to a variant of a parent strain, and methods of obtaining a mutant or variant, wherein the pesticide activity is greater than the pesticide activity expressed by the parent strain. The "parent strain" herein is defined as the original strain before mutagenesis. To obtain such mutants, the parent strain can be treated with chemicals such as N-methyl-N'-nitro-N-nitrosoguanidine, ethyl methyl sulfone, or irradiated with gamma rays, x-rays or ultraviolet rays, or other methods well known to those skilled in the art. Known mechanisms of biological control agents include enteric bacteria that control root rot by competing for space with fungi on the root surface. Bacterial toxins (such as antibiotics) have been used to control pathogens. The toxins can be isolated and applied directly to the plant, or bacterial species can be applied so that they produce the toxin in situ.

[0179] A "variant" is a strain having all of the identifying characteristics of an NRRL or ATCC accession number as set forth herein and can be identified as having a genome that hybridizes under high stringency conditions to the genome of the NRRL or ATCC accession number.

[0180] "Hybridization" refers to a reaction in which one or more polynucleotides react to form a complex stabilized by hydrogen bonds between nucleotide residues. Hydrogen bonds can occur by Watson-Crick base pairing, Hoogstein binding, or any other sequence-specific means. The complex can contain two chains forming a double-stranded structure, three or more chains forming a multi-stranded complex, a single self-hybridizing chain, or any combination of these. Hybridization reactions can be performed under different "rigorous" conditions. Typically, low-rigor hybridization reactions are performed in 10X SSC at about 40°C or in a solution of equivalent ionic strength / temperature. Ordinary stringent hybridizations are typically performed in 6X SSC at about 50°C, while high-rigor hybridization reactions are typically performed in 1X SSC at about 60°C.

[0181] Variants of a designated NRRL or ATCC accession number may also be defined as strains having a genomic sequence that is greater than 85%, more preferably greater than 90%, or more preferably greater than 95% identical in sequence to the genome of the designated NRRL or ATCC accession number. A polynucleotide or polynucleotide region (or a polypeptide or polypeptide region) having a certain percentage (e.g., 80%, 85%, 90%, or 95%) of "sequence identity" to another sequence means that, when aligned, the two sequences being compared have that percentage of bases (or amino acids) that are the same. Such alignments and percentages of homology or sequence identity may be determined using software programs known in the art, such as those described in Current Protocols in Molecular Biology (FM Ausubel et al., eds., 1987).

[0182] NRRL is the abbreviation of Agricultural Research Service Culture Collection. According to the Budapest Treaty on the International Recognition of the Deposit of Microorganisms for the Purposes of Patent Procedure, this organization is an international depository institution established for the purpose of depositing microbial strains. Its address is National Center for Agricultural Utilization Research, Agricultural Research service, USDepartment of Agriculture, 1815 North University Street, Peroira, Illinois 61604 USA.

[0183] ATCC is the abbreviation of American Type Culture Collection. According to the Budapest Treaty on the International Recognition of the Deposit of Microorganisms for the Purposes of Patent Procedure, this organization is an international depository established for the purpose of depositing microbial strains. Its address is ATCC Patent Depository, 10801 University Blvd., Manassas, VA 10110 USA.

[0184] Examples of biological control agents that can be combined with the compounds and compositions of the present invention are:

[0185] (A) an antibacterial agent selected from the group consisting of:

[0186] (A1) Bacteria, such as (A1.01) Bacillus subtilis, in particular strain QST713 / AQ713 (available from Bayer CropScience LP, US as SERENADE OPTI or SERENADE ASO, NRRL registration number B21661, US Patent No. 6,060,051); (A1.02) Bacillus sp., in particular strain D747 (available from Kumiai Chemical Industry Co., Ltd. as DOUBLE (A1.03) Bacillus pumilus, in particular strain BUF-33, NRRL Accession No. 50185 (available from BASF as Product, EPA registration number 71840-19); (A1.04) Bacillus subtilis var. amyloliquefaciens strain FZB24, registration number DSM 10271 (available from Novozymes as or ECO (EPA registration number 70127-5)); (A1.05) Paenibacillus sp. strain, registration number NRRL B-50972 or registration number NRRL B-67129, WO 2016 / 154297; (A1.06) Bacillus subtilis strain BU1814, (available from BASF SE as PLUS, FLEX and EXTRA); (A1.07) Bacillus mojavensis strain R3B (accession number NCAIM (P) B001389) (WO 2013 / 034938) from Certis USA LLC (a subsidiary of Mitsui & Co.); (A1.08) Bacillus subtilis CX-9060 from Certis USA LLC (a subsidiary of Mitsui & Co.); (A1.09) Paenibacillus polymyxa, in particular strain AC-1 (e.g. from Green Biotech Company Ltd. ); (A1.10) Pseudomonas proradix (e.g. from Sourcon Padena ); (A1.11) Pantoea agglomerans, in particular strain E325 (accession number NRRL B-21856) (available from Northwest Agri Products as BLOOMTIME BIOLOGICALTM FDBIOPESTICIDE); and

[0187] (A2) Fungi, such as (A2.01) Aureobasidium pullulans, in particular blastospores of strain DSM 14940, blastospores of strain DSM 14941, or a mixture of blastospores of strains DSM 14940 and DSM 14941 (e.g. from bio-ferm, CH and BLOSSOM ); (A2.02) Pseudozyma aphidis (as disclosed by Yissum Research Development Company of the Hebrew University of Jerusalem in WO 2011 / 151819); (A2.03) Saccharomyces cerevisiae, in particular strains CNCM No. I-3936, CNCM No. I-3937, CNCM No. I-3938 or CNCM No. I-3939 from Lesaffre et Compagnie, FR (WO 2010 / 086790);

[0188] (B) a biofungicide selected from the group consisting of:

[0189] (B1) bacteria, for example (B1.01) Bacillus subtilis, in particular strain QST713 / AQ713 (available from Bayer CropScience LP, US as SERENADE OPTI or SERENADE ASO, NRRL accession number B21661 and described in US Pat. No. 6,060,051); (B1.02) Bacillus pumilus, in particular strain QST2808 (available from Bayer CropScience LP, US as (B1.03) Bacillus pumilus, in particular strain GB34 (available from Bayer AG, DE as Yield (B1.04) Bacillus pumilus, in particular strain BU F-33, NRRL registration number 50185 (available from BASF as part of the CARTISSA product, EPA registration number 71840-19); (B1.05) Bacillus amyloliquefaciens, in particular strain D747 (available from Kumiai Chemical Industry Co., Ltd. as Double Nickel TM (B1.06) Bacillus subtilis Y1336 (available from Bion-Tech, Taiwan, China, with registration number FERM BP-8234, U.S. Patent No. 7,094,592); WP, registered as a biofungicide in Taiwan under registration numbers 4764, 5454, 5096 and 5277); (B1.07) Bacillus subtilis strain MBI 600 (available from BASF SE as SUBTILEX), registration number NRRL B-50595, U.S. Patent No. 5,061,495; (B1.08) Bacillus subtilis strain GB03 (available from Bayer AG, DE as (B1.09) Bacillus subtilis var. amyloliquefaciens strain FZB24, registration number DSM 10271 (available from Novozymes as or ECO (EPA Accession No. 70127-5)); (B1.10) Bacillus mycoides, isolate J, Accession No. B-30890 (available from Certis USA LLC (a subsidiary of Mitsui & Co.) as BMJ or WG and LifeGardTM); (B1.11) Bacillus licheniformis, in particular strain SB3086, accession number ATCC 55406, WO 2003 / 000051 (available from Novozymes as Biofungicide and GREEN RELEAFTM); (B1.12) Paenibacillus sp. strain, registration number NRRL B-50972 or registration number NRRL B-67129, WO 2016 / 154297; (B1.13) Bacillus subtilis strain BU1814, (available from BASF SE as PLUS, FLEX and EXTR); (B1.14) Bacillus subtilis CX-9060 from Certis USA LLC (a subsidiary of Mitsui & Co.); (B1.15) Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL Accession No. B-50768; WO 2014 / 028521) (from Marrone Bio Innovations ); (B1.16) Bacillus amyloliquefaciens strain FZB42, registration number DSM 23117 (available from ABiTEP, DE (B1.17) Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (from FMC (WG) and (WP)); (B1.18) Bacillus mohaiwei strain R3B from Certis USALLC (a subsidiary of Mitsui & Co.) (registration number NCAIM (P) B001389) (WO2013 / 034938); (B1.19) ssp. plantarum from BASF SE (WO2016 / 020371); (B1.20) Paenibacillus epiphyticus from BASF SE (WO2016 / 020371); (B.1.21) Pseudomonas chlororaphis strain AFS009, registration number NRRL B-50897, WO 2017 / 019448 (e.g. HOWLER from AgBiome Innovations, US TM and ); (B1.22) Pseudomonas chlororaphis, in particular strain MA342 (eg, provided by Bioagri and Koppert and ); (B1.23) Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (from Novozymes and ); (B1.24) Agrobacterium radiobacter strain K84 (e.g. from AgBioChem, CA ); (B1.25) radiobacterium strain K1026 (e.g. NOGALLTM from BASF SE); (B1.26) Bacillus subtilis KTSB strain (from Donaghys ); (B1.27) Bacillus subtilis IAB / BS03 (AVIV™ from STK Bio-Ag Technologies); (B1.28) Bacillus subtilis strain Y1336 (available from Bion-Tech, Taiwan, China WP, registered as a biofungicide in Taiwan under registration numbers 4764, 5454, 5096 and 5277); (B1.29) Bacillus amyloliquefaciens isolate B246 (e.g. AVOGREENTM from University of Pretoria); (B1.30) Bacillus methylotrophicus strain BAC-9912 (from Chinese Academy of Sciences' Institute of Applied Ecology); (B1.31) Pseudomonas proradix (e.g. from Sourcon Padena ); (B1.32) Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (accession number DSM 7206) (from Verdera From BioWorks See Crop Protection 2006, 25, 468-475); (B1.33) Pseudomonas fluorescens strain A506 (e.g. provided by NuFarm );and

[0190] (B2) Fungi, for example: (B2.01) Coniothyrium minitans, in particular strain CON / M / 91-8 (registration number DSM-9660; e.g. ); (B2.02) Metschnikowia fructicola, in particular strain NRRL Y-30752; (B2.03) Microsphaeropsis ochracea; (B2.04) Trichoderma atroviride, in particular strain SC1 (accession number CBS122089, WO 2009 / 116106 and U.S. Pat. No. 8,431,120 (from Bi-PA)), strain 77B (T77 from Andermatt Biocontrol) or strain LU132 (e.g. Sentinel from Agrimm Technologies Limited); (B2.05) Trichoderma harzianum strain T-22 (e.g. Trianum-P from Andermatt Biocontrol or Koppert) or strain Cepa Simb-T5 (from Simbiose Agro); (B2.06) Gliocladium roseum (also known as Clonostachys rosea f. rosea), in particular strain 321U from Adjuvants Plus, strain ACM941 disclosed in Xue (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea, Can Jour Plant Sci 83(3):519-524), or strain IK726 (Jensen DF et al. Development of a biocontrol agent for plant disease control with special emphasis on the near commercial fungal antagonist Clonostachys rosea strain 'IK726'; Australas Plant Pathol. 2007; 36:95-101); (B2.07) Talaromyces flavus), strain V117b; (B2.08) Trichoderma viride, in particular strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161: 125-137); (B2.09) Trichoderma asperellum, in particular strain SKT-1, registration number FERM P-16510 (eg from Kumiai Chemical Industry. ), strain T34 (e.g. T34 Biocontrol provided by Biocontrol Technologies S.L., ES) or strain ICC 012 from Isagro; (B2.10) Trichoderma aureum, strain CNCM I-1237 (e.g. from Agrauxine, FR WP); (B2.11) dark green Trichoderma, strain number V08 / 002387; (B2.12) dark green Trichoderma, strain NMI number V08 / 002388; (B2.13) dark green Trichoderma, strain NMI number V08 / 002389; (B2.14) dark green Trichoderma, strain NMI number V08 / 002390; (B2.15) dark green Trichoderma, strain LC52 (e.g., Tenet provided by Agrimm Technologies Limited); (B2.16) dark green Trichoderma, strain ATCC 20476 (IMI206040); (B2.17) Trichoderma aureum, strain T11 (IMI352941 / CECT20498); (B2.18); Trichoderma harmatum; (B2.19) Trichoderma harzianum; (B2.20) Trichoderma harzianum rifai T39 (e.g. from Makhteshim, US ); (B2.21) Trichoderma acanthosporum, in particular strain kd (e.g. T-Gro from Andermatt Biocontrol); (B2.22) Trichoderma harzianum, strain ITEM 908 (e.g. Trianum-P from Koppert); (B2.23) Trichoderma harzianum, strain TH35 (e.g. Root-Pro provided by Mycontrol); (B2.24) Trichoderma virens (also known as Gliocladium virens), in particular strain GL-21 (e.g. SoilGard provided by Certis, US); (B2.25) Trichoderma viride, strain TV1 (e.g. Trianum-P provided by Koppert); (B2.26) Ampelomyces quisqualis, in particular strain AQ 10 (e.g. AQ ); (B2.27) budding mold, in particular spores of strain DSM 14940; (B2.28) budding mold, in particular spores of strain DSM 14941; (B2.29) budding mold, in particular a mixture of spores of strains DSM 14940 and DSM 14941 (e.g. provided by bio-ferm, CH ); (B2.30) Cladosporium cladosporioides, strain H39, registration number CBS122244, US2010 / 0291039 (provided by Stichting Dienst Landbouwkundig Onderzoek); (B2.31) Gliocladiumcatenulatum (synonym: Clonostachys roseaf.catenulate) strain J1446 (provided by Lallemand, for example). ); (B2.32) conidia of Lecanicillium lecanii (formerly Verticillium lecanii) strain KV01 (e.g. provided by Koppert / Arysta ); (B2.33) Penicillium vermiculatum; (B2.34) Pichia anomala, strain WRL-076 (NRRL Y-30842), U.S. Patent No. 7,579,183; (B2.35) Trichoderma viridis, strain SKT-1 (FERM P-16510), Japanese Patent Publication (Kokai) No. 11-253151A; (B2.36) Trichoderma viridis, strain SKT-2 (FERM P-16511), Japanese Patent Publication (Kokai) No. 11-253151A; (B2.37) Trichoderma viridis, strain SKT-3 (FERM P-17021), Japanese Patent Publication (Kokai) No. 11-253151A; (B2.38) Trichoderma geimersi gamsii) (formerly T. viride), strain ICC080 (IMICC 392151CABI, for example BioDerma provided by AGROBIOSOL DE MEXICO, SADE CV); (B2.39) Trichoderma harzianum, strain DB103 (available as T-Gro 7456 from Dagutat Biolab); (B2.40) Trichoderma polysporum, strain IMI 206039 (for example Binab TF WP provided by BINAB Bio-Innovation AB, Sweden); (B2.41) Trichoderma stromaticum, accession number Ts3550 (for example Tricovab provided by CEPLAC, Brazil); (B2.42) Ulocladium oudemansii strain U3, accession number NM 99 / 06216 (for example provided by Botry-Zen Ltd, New Zealand and from BioWorks, Inc. ); (B2.43) Verticillium albo-atrum (formerly V. dahliae), strain WCS850 with accession number WCS850, deposited in the Central Bureau for Fungi Cultures (e.g. DUTCH provided by Tree Care Innovations ); (B2.44) Verticillium chlamydosporium; (B2.45) a mixture of Trichoderma aculeatus strain ICC 012 (also known as Trichoderma harzianum ICC012) (accession number CABI CC IMI 392716) and Trichoderma gemsii strain (formerly T. viride) strain ICC080 (accession number IMI 392151) (e.g., BIO-TAM™ from Isagro USA, Inc. and provided by Agrobiosolde Mexico, SA de CV ); (B2.46) Trichoderma asperelloides JM41R (registration number NRRL B-50759) (TRICHO from BASF SE ); (B2.47) Aspergillus flavus strain NRRL 21882 (from Syngenta / ChemChina known as (B2.48) Chaetomium cupreum (registration number CABI 353812) (e.g. BIOKUPRUMTM provided by AgriLife); (B2.49) Saccharomyces cerevisiae, in particular strain LASO2 (from Agro-Levureset Dérivés), strain LAS117 cell wall (from Lesaffre From BASF SE ), strains CNCM No. I-3936, CNCM No. I-3937, CNCM No. I-3938, CNCM No. I-3939 from Lesaffre et Compagnie, FR (WO 2010 / 086790); (B2.50) Trichoderma virens strain G-41, previously also known as Gliocladium virens (accession number ATCC 20906) (e.g., from BioWorks, US PLUS WP and PLUS WP); (B2.51) Trichoderma hamatum, accession number ATCC28012; (B2.52) Psoralea corylifolia strain AQ10, accession number CNCM I-807 (e.g., AQ ); (B2.53) Phlebiopsis gigantea strain VRA 1992 (from Danstar Ferment C); (B2.54) Penicillium steckii from BASF SE (DSM 27859; WO 2015 / 067800); (B2.55) Chaetomium globosum (available from Rivale (B2.56) Cryptococcus flavescens, strain 3C (NRRL Y-50378); (B2.57) Dactylaria candida; (B2.58) Dilophosphora alopecuri (can TWIST (B2.59) Fusarium oxysporum, strain Fo47 (available from NaturalPlant Protection (B2.60) Pseudozyma flocculosa, strain PF-A22 UL (available from Plant Products Co., CA L); (B2.61) Trichoderma gemsii (formerly T. viride), strain ICC 080 (IMI CC 392151 CABI) (provided by AGROBIOSOL DEMEXICO, SADE CV (B2.62) Trichoderma fertile (e.g. the product TrichoPlus from BASF); (B2.63) Muscodor roseus, in particular strain A3-5 (registration number NRRL 30548); (B2.64) Simplicillium lanosoniveum;

[0191] (C) Biological control agents having the effect of improving plant growth and / or plant health, which can be combined with the compound combination of the present invention, include:

[0192] (C1) Bacteria selected from the group consisting of: (C1.01) Bacillus pumilus, in particular strain QST2808 (NRRL registration number B-30087); (C1.02) Bacillus subtilis, in particular strain QST713 / AQ713 (NRRL registration number B-21661 and described in U.S. Pat. No. 6,060,051; (C1.03) available from Bayer CropScience LP, US Opti or ASO); (C1.04) Bacillus subtilis, in particular strain AQ30002 (accession number NRRL B-50421 and described in U.S. patent application Ser. No. 13 / 330,576); (C1.05) Bacillus subtilis, in particular strain AQ30004 (NRRL B-50455 and described in U.S. patent application Ser. No. 13 / 330,576); (C1.06) Sinorhizobium meliloti strain NRG-185-1 (from Bayer CropScience GOLD); (C1.07) Bacillus subtilis strain BU1814, (available from BASF SE as (obtained from Biofilm Crop Protection); (C1.08) Bacillus subtilis rm303 (obtained from ); (C1.09) Bacillus amyloliquefaciens pm414 (from Biofilm Crop Protection ); (C1.10) Bacillus mycoides BT155 (NRRL No. B-50921), Bacillus mycoides EE118 (NRRL No. B-50918), (C1.11) Bacillus mycoides EE141 (NRRL No. B-50916), (C1.12) Bacillus mycoides BT46-3 (NRRL No. B-50922), (C1.13) Bacillus cereus family member EE128 (NRRL No. B-50917), (C1.14) Bacillus thuringiensis (Bacillus thuringiensis) BT013A (NRRL No. B-50924) (also known as Bacillus thuringiensis 4Q7), (C1.15) Bacillus cereus family member EE349 (NRRL No. B-50928), (C1.16) Bacillus amyloliquefaciens SB3281 (ATCC #PTA-7542; WO 2017 / 205258), (C1.17) Bacillus amyloliquefaciens TJ1000 (available from Novozymes as (C1.18) Bacillus firmus, in particular strain CNMC I-1582 (e.g. from BASF SE ); (C1.19) Bacillus pumilus, in particular strain GB34 (e.g. YIELD from Bayer Crop Science, DE ); (C1.20) Bacillus amyloliquefaciens, in particular strain IN937a; (C1.21) Bacillus amyloliquefaciens, in particular strain FZB42 (e.g. from ABiTEP, DE ); (C1.22) Bacillus amyloliquefaciens BS27 (registration number NRRL B-5015); (C1.23) a mixture of Bacillus moss FMCH001 and Bacillus subtilis FMCH002 (available from FMC Corporation as (WG), (WP) obtained); (C1.24) Bacillus cereus, in particular strain BP01 (ATCC 55675; e.g. from Arysta Lifescience, US ); (C1.25) Bacillus subtilis, in particular strain MBI 600 (e.g. from BASF SE ); (C1.26) Bradyrhizobium japonicum (e.g., from Novozymes ); (C1.27) Mesorhizobium cicer (e.g. NODULATOR from BASF SE); (C1.28) Rhizobium leguminosarium biovar viciae (e.g. NODULATOR from BASF SE); (C1.29) Delftia acidovorans, in particular strain RAY209 (e.g. ); (C1.30) Lactobacillus sp. (e.g. from LactoPAFI ); (C1.31) Bacillus polymyxa, in particular strain AC-1 (e.g. from GreenBiotech Company Ltd. ); (C1.32) Pseudomonas proradix (e.g. from Sourcon Padena ); (C1.33) Azospirillum brasilense (e.g., from KALO, Inc. ); (C1.34) Azospirillum lipoferum (e.g., VERTEX-IFTM from TerraMax, Inc.); (C1.35) a mixture of Azotobactervinelandii and Clostridium pasteurianum (available from Agrinos (C1.36) Pseudomonas aeruginosa, in particular strain PN1; (C1.37) Rhizobium leguminosarum, in particular bv. viceae strain Z25 (accession number CECT 4585); (C1.38) Azorhizobium caulinodans, in particular strain ZB-SK-5; (C1.39) Azotobacter chroococcum, in particular strain H23; (C1.40) Azotobacter chroococcum, in particular strain ATCC12837; (C1.41) Bacillus siamensis, in particular strain KCTC 13613T; (C1.42) Bacillus tequila tequilensis), in particular strain NII-0943; (C1.43) Serratia marcescens, in particular strain SRM (accession number MTCC 8708); (C1.44) Thiobacillus sp. (e.g. from Cropaid Ltd UK );and

[0193] (C2) fungi selected from the group consisting of: (C2.01) Purpureocillium lilacinum (formerly Paecilomyces lilacinus) strain 251 (AGAL 89 / 030550; e.g. BioAct from Bayer Crop Science Biologics GmbH) Penicillium bilaii, (C2.02) strain ATCC 22348 (e.g. BioAct from Acceleron BioAg ), (C2.03) Demodex flavus, strain V117b; (C2.04) Trichoderma virens strain CNCM I-1237 (e.g. from Agrauxine, FR WP), (C2.05) viride, such as strain B35 (Pietr et al., 1993, Zesz. Nauk. A Rw Szczecinie 161: 125-137); (C2.06) Trichoderma aureum strain LC52 (also known as Trichoderma aureum strain LU132; for example, Sentinel from Agrimm Technologies Limited); (C207.) Trichoderma aureum strain SC1 described in International Application No. PCT / IT2008 / 000196; (C2.08) Trichoderma aculeatus strain kd (for example, T-Gro from Andermatt Biocontrol); (C2.09) Trichoderma aculeatus strain Eco-T (Plant Health Products, ZA); (C2.10) Trichoderma harzianum strain T-22 (for example, from Andermatt Biocontrol); Biocontrol or Koppert's Trianum-P); (C2.11) Myrothecium verrucaria strain AARC-0255 (e.g. DiTera from Valent Biosciences TM ); (C2.12) Penicillium strain ATCC ATCC20851; (C2.13) Pythium oligandrum strain M1 (ATCC 38472; for example, Polyversum from Bioprepraty, CZ); (C2.14) Trichoderma virens strain GL-21 (for example, from Certis, USA ); (C2.15) Verticillium dahliae (formerly V. dahliae) strain WCS850 (CBS276.92; for example Dutch Trig from Tree Care Innovations); (C2.16) Trichoderma aureum, in particular strain number V08 / 002387, strain number NMI number V08 / 002388, strain number NMI number V08 / 002389, strain number NMI number V08 / 002390; (C2.17) Trichoderma harzianum strain ITEM 908; (C2.18) Trichoderma harzianum, strain TSTh20; (C2.19) Trichoderma harzianum strain 1295-22; (C2.20) Pythium oligandrum strain DV74; (C2.21) Rhizopogon amylopogon (for example contained in Chemical Company); (C2.22) Rhizopogon fulvigleba (e.g. contained in Myco-Sol from Helena Chemical Company); and (C2.23) Trichoderma virens strain GI-3;

[0194] (D) insecticidal biological control agents selected from:

[0195] (D1) A bacterium selected from the group consisting of: (D1.01) Bacillus thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372; e.g., from Valent BioSciences ); (D1.02) Bacillus mycoides, isolate J. (e.g., BmJ from Certis USALLC (a subsidiary of Mitsui & Co.)); (D1.03) Bacillus sphaericus, in particular serotype H5a5b strain 2362 (strain ABTS-1743) (e.g., from Valent BioSciences, US ); (D1.04) Bacillus thuringiensis subsp. kurstaki strain BMP 123 from Becker Microbial Products, IL; (D1.05) Bacillus thuringiensis subsp. ayuzawa, in particular serotype H-7 (e.g., from Valent BioSciences, US WG); (D1.06) Bacillus thuringiensis subsp. Kurstaki strain HD-1 (e.g., from Valent BioSciences, US ES); (D1.07) Bacillus thuringiensis subsp. Kurstaki strain BMP 123 provided by Becker Microbial Products, IL; (D1.08) Bacillus thuringiensis israelensis strain BMP 144 (e.g., provided by Becker Microbial Products IL ); Burkholderia spp., in particular (D1.09) Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (accession number NRRL B-50319; WO 2011 / 106491 and WO 2013 / 032693; for example MBI-206TGAI and ); (D1.10) active purple bacteria (Chromobacterium subtsugae), in particular strain PRAA4-1T (MBI-203; e.g. from Marrone Bio Innovations ); (D1.11) Paenibacillus popilliae (formerly Bacillus popilliae; for example, MILKY SPORE POWDERTM and MILKY SPOREGRANULARTM from St.Gabriel Laboratories); (D1.12) Bacillus thuringiensis subsp. israelensis (serotype H-14) strain AM65-52 (accession number ATCC 1276) (for example, provided by Valent BioSciences, US ); (D1.13) Bacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., from AEF Global ); (D1.14) Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428; e.g. from BioFa DE FC); (D1.15) Bacillus thuringiensis var. japonensis strain Buibui; (D1.16) Bacillus thuringiensis subsp. Kurstaki strain ABTS 351; (D1.17) Bacillus thuringiensis subsp. Kurstaki strain PB 54; (D1.18) Bacillus thuringiensis subsp. Kurstaki strain SA 11; (D1.19) Bacillus thuringiensis subsp. Kurstaki strain SA 12; (D1.20) Bacillus thuringiensis subsp. Kurstaki strain EG 2348; (D1.21) Bacillus thuringiensis var. Colmeri (for example, TIANBAOBTC provided by Changzhou Jianghai Chemical Factory); (D1.22) Bacillus thuringiensis subsp. Ayuzawa strain GC-91; (D1.23) Serratia entomophila (for example, provided by Wrightson Seeds Provided ); (D1.24) Serratia marcescens, in particular strain SRM (accession number MTCC8708); and (D1.25) Wolbachia pipientis ZAP strain (e.g., ZAP from MosquitoMate );and

[0196] (D2) A fungus selected from the group consisting of: (D2.01) Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus) strain apopka 97; (D2.02) Beauveria bassiana strain ATCC 74040 (e.g., from Intrachem Bio Italia) ); (D2.03) Beauveria bassiana strain GHA (Accession No. ATCC 74250; e.g., from Laverlam International Corporation ES and ); (D2.04) Zoophtora radicans; (D2.05) Metarhizium robertsii 15013-1 (deposited under NRRL Accession No. 67073), (D2.06) Metarhizium robertsii 23013-3 (deposited under NRRL Accession No. 67075), and (D2.07) Metarhizium anisopliae 3213-1 (deposited under NRRL Accession No. 67074) (WO2017 / 066094; Pioneer Hi-Bred International); (D2.08) Beauveria bassiana strain ATP02 (Accession No. DSM 24665);

[0197] (E) a virus selected from the group consisting of Adoxophyes orana (summer fruit tortrix) granulovirus (GV), Cydia pomonella (codling moth) granulovirus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV and Spodoptera littoralis (African cotton leafworm) NPV;

[0198] (F) Bacteria and fungi which can be added to plants or plant parts or plant organs as "inoculants" and which, by virtue of their specific properties, promote plant growth and plant health. Examples of such bacteria and fungi are: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp. or Gigasporamonosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., in particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp. and Streptomyces spp.; and

[0199] (G) Plant extracts and products formed by microorganisms (including proteins and secondary metabolites) that can be used as biological control agents, such as Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), pyrethrum / pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, "Requiem TM "Insecticides", rotenone, ryania / ryanodine, Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, extracts of the Brassicaceae family (especially rapeseed powder or mustard powder), and biological insecticidal / acaricidal active substances obtained from olive oil, especially those with a carbon chain length of C 16 -C 20 Unsaturated fats / carboxylic acids as active ingredients, such as those contained in the trade name products.

[0200] The compounds and compositions of the present invention may be combined with one or more active ingredients selected from the group consisting of insecticides, acaricides and nematicides.

[0201] "Insecticides" and the term "insecticidal" refer to a substance that increases the mortality of insects or inhibits their growth rate. As used herein, the term "insects" includes all organisms in the class "insecta".

[0202] "Nematicide" and "nematicidal" refer to a substance that increases mortality or inhibits the growth rate of nematodes. In general, the term "nematode" encompasses eggs, larvae, young, and mature forms of the organism.

[0203] "Acaricide" and "acaricidal" refer to a substance that increases the mortality or inhibits the growth rate of ectoparasites belonging to the class Arachnida, subclass Acari.

[0204] Examples of insecticides, acaricides and nematicides that can be mixed with the compounds and compositions of the present invention are:

[0205] (1) an acetylcholinesterase (AChE) inhibitor, preferably a carbamate selected from the group consisting of alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb ), isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or an organophosphate selected from acephate, azamethiphos, azinphos-ethyl and thiocarb. phos-ethyl), azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chloropyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate thoate), dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imiciafos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion,Malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, piriphos miphos-methyl), profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon, and vamidothion.

[0206] (2) GABA-gated chloride channel blockers, preferably cyclopentadienyl organochlorines selected from chlordane and endosulfan; or phenylpyrazoles (fiproles) selected from ethiprole and fipronil.

[0207] (3) Sodium channel modulators, preferably pyrethroids, selected from acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer,isomer), bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cyfluthrin, -cypermethrin), theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans-isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenpro x), fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(1R)-trans isomer] (phenothrin [( 1R)-trans-isomer]), prallethrin, pyrethrine, pyrethrum, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin and transfluthrin; or DDT; or methoxychlor.

[0208] (4) Competitive modulators of nicotinic acetylcholine receptors (nAChR), preferably neonicotinoids selected from acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoximines selected from sulfoxaflor; or butenolids selected from flupyradifurone; or mesoionics selected from triflumezopyrim.

[0209] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators (site I), preferably spinosyns, selected from spinetoram and spinosad.

[0210] (6) Allosteric modulators of glutamate-gated chloride channels (GluCl), preferably avermectins / milbemycins, selected from abamectin, emamectin benzoate, lepimectin and milbemectin.

[0211] (7) Juvenile hormone mimetics, preferably juvenile hormone analogs, selected from hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

[0212] (8) Various non-specific (multi-site) inhibitors, preferably alkyl halides selected from methyl bromide and other alkyl halides; or chloropicrine or sulfuryl fluoride or borax or tartar emetic or methyl isocyanate generators selected from diazomet or metam.

[0213] (9) String organ TRPV channel modulators, preferably pyridine azomethane and pyrifluquinazone selected from pymetrozine, or pyropene selected from afidopyropen.

[0214] (10) A mite growth inhibitor affecting CHS1 selected from clofentezine, hexythiazox and diflovidazin or etoxazole.

[0215] (11) A microbial disruptor of insect gut membranes, selected from Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and Bt plant proteins, selected from Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb and Cry34Ab1 / 35Ab1.

[0216] (12) Inhibitors of mitochondrial ATP synthase, preferably ATP disruptors, selected from diafenthiuron or organotin compounds selected from azoxatin, cyclohexidine and fenbutatin oxide or propargite or tetradifon.

[0217] (13) An uncoupler of oxidative phosphorylation by blocking the proton gradient, selected from chlorfenapyr, dinitrocresol (DNOC) and sulphluramid.

[0218] (14) A nicotinic acetylcholine receptor channel blocker selected from the group consisting of bensultap, cartap hydrochloride, thiocyclam and thiosultap-sodium.

[0219] (15) Chitin biosynthesis inhibitors, affecting CHS1, preferably selected from the benzoylurea class of bistrifluron, chlofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

[0220] (16) Chitin biosynthesis inhibitors, type 1, selected from buprofezin.

[0221] (17) Molting disruptors (particularly for Diptera, i.e. dipterans), selected from cyromazine.

[0222] (18) Ecdysone receptor agonists, preferably diacylhydrazines selected from chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0223] (19) An octopamine receptor agonist selected from amitraz.

[0224] (20) A mitochondrial complex III electron transport inhibitor selected from the group consisting of hydramethylnone, acequinocyl, fluacrypyrim and bifenazate.

[0225] (21) Mitochondrial complex I electron transport inhibitors, preferably METI miticides and insecticides selected from fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad; or rotenone (Derris).

[0226] (22) Voltage-dependent sodium channel blockers, preferably oxadiazine selected from indoxacarb and semicarbazone selected from metaflumizone.

[0227] (23) Inhibitors of acetyl CoA carboxylase, preferably tetronic acid and tetramic acid derivatives selected from spirodiclofen, spiromesifen, spiropidion and spirotetramat.

[0228] (24) Mitochondrial complex IV electron transport inhibitors, preferably phosphides selected from aluminum phosphide, calcium phosphide, phosphine and zinc phosphide, or cyanides selected from calcium cyanide, potassium cyanide and sodium cyanide.

[0229] (25) Mitochondrial complex II electron transport inhibitors, preferably β-ketonitrile derivatives selected from cyenopyrafen and cyflumetofen or carboxanilides selected from pyflubumide.

[0230] (28) A nicotinic acid receptor modulator, preferably a diamide selected from the group consisting of chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide and tetraniliprole.

[0231] (29) A chord organ modulator (with undefined target site) selected from flonicamid.

[0232] (30) An allosteric modulator of a GABA-gated chloride channel, preferably a diamide selected from bromofluoroaniline or an isoxazole selected from fluxametamide.

[0233] (31) Baculovirus, preferably a granulovirus (GVs) selected from the group consisting of Cydia pomonella GV and Thaumatotibialeucotreta (GV) or a nuclear polyhedrosis virus (NPV) selected from the group consisting of Anticarsia gemmatalis MNPV, Flucypyriprole and Helicoverpa armigera NPV.

[0234] (32) An allosteric modulator of the nicotinic acetylcholine receptor (site II) selected from the group consisting of GS-ω / κ-HXTX-Hv1a peptide.

[0235] (33) Other active ingredients selected from the group consisting of: Acynonapyr, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Benzpyrimoxan, Bromopropylate, Chinomethionat, Chloroprallethrin, Cryolite, Cyclobutrifluram, Cycloxaprid, Cyetpyrafen, Cyhalodiamide, Cyproflanilide (CAS 2375110-88-4), Dicloromezotiaz, Dicofol, Dimpropyridaz, Epsilon-Metofluthrin, Epsilon-Momfluthrin, Flometoquin, Fluazaindolizine, Flucypyriprole (CAS1771741-86-6), Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Flupyrimin, Fluralaner, Fufenozide, Flupentiofenox, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, Isocycloseram, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner, Cyprodinil (Meperfluthrin), Nicofluprole (CAS1771741-86-6), Oxazosulfyl, Paichongding, Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Sarolaner, Spidoxamat, Spirobudiclofen, Tetramethylfluthrin, Tetrachlorantraniliprole, Tigolaner, Tioxazafen, Thiofluoximate, Tyclopyrazoflor, iodomethane); and Bacillus firmus (Bacillus firmus) (I-1582, Votivo) azadirachtin (BioNeem) and the following compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO2006 / 043635) (CAS 885026-50-6), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006 / 003494) (CAS872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO2010052161) (CAS1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethyl carbonate (known from EP2647626) (CAS1440516 -42-6), PF1364 (known from JP2010 / 018586) (CAS1204776-60-2), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoro-propan-2-one (known from WO2013 / 144213) (CAS1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H- Pyrazole-5-carboxamide (known from WO2010 / 051926) (CAS1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (known from CN103232431) (CAS1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N- (cis-1-oxo-3-thietanyl)-benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxo-3-thietanyl)-benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxo-3-thietanyl)benzamide (from WO2013 / 050317 A1 known) (CAS 1332628-83-7), N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide, (+)-N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide and (-)-N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide (known from WO 2013 / 162715 A2, WO 2013 / 162716A2, US2014 / 0213448A1 known) (CAS1477923-37-7), 5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile (known from CN 101337937 A) (CAS1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thiomethyl]phenyl]-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (Liudaibenjiaxuanan, known from CN103109816 A known) (CAS 1232543-85-9); N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO 2012 / 034403 A1) (CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (known from WO 2011 / 085575 A1) (CAS 1233882-22-8), 4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)-pyrimidine (known from CN 101337940 A) (CAS 1108184-52-6); (2E)- and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide (known from CN101715774 A) (CAS 1232543-85-9); 3-(2,2-dichlorovinyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenylcyclopropanecarboxylate (known from CN 103524422 A known from (CAS 1542271-46-4); (4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]-indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2); 6-deoxy-3-O-ethyl-2,4-di-O-methyl-1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]carbamate]-α-L-pyranose (known from US2014 / 0275503A1 known) (CAS1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS1253850-56-4), (8-trans)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS 933798-27-7), (8-cis)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8), N-[4-(aminothiomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (known from CN103265527 A) (CAS 1452877-50-7), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decane-2,4-dione (known from WO 2014 / 187846 A1) (CAS 1638765-58-8), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl carbonate (known from WO 2010 / 066780 A1, WO 2011151146 A1) (CAS 1229023-00-0), N-[1-(2,6-difluorophenyl)-1H-pyrazole-3-yl]-2-(trifluoromethyl)benzamide (known from WO 2014 / 053450 A1) (CAS 1594624-87-9), N-[2-(2,6-difluorophenyl)-2H-1,2,3-triazole-4-yl]-2-(trifluoromethyl)benzamide (known from WO 2014 / 053450 A1) (CAS 1594637-65-6), N-[1-(3,5-difluoro-2-pyridine)-1H-pyrazole-3-yl]-2-(trifluoromethyl)benzamide (known from WO 2014 / 053450 A1) (CAS 1594626-19-3), (3R)-3-(2-chloro-5-thiazole)-2,3-dihydro-8-methyl-5,7-dioxa-6-phenyl-5H-thiazolo[3,2-a]pyrimidine inner salt (known from WO 2018 / 177970A1) (CAS2246757-58-2); 3-(2-chloro-5-thiazole)-2,3-dihydro-8-methyl-5,7-dioxa-6-phenyl-5H-thiazolo[3,2-a]pyrimidine inner salt (known from WO 2018 / 177970 A1) (CAS 2246757-56-0); N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-2-(methylsulfonyl)propionamide (known from WO 2019 / 236274 A1) (CAS 2396747-83-2); N-[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-2-fluoro-3-[(4-fluorobenzyl)amino]benzamide (known from WO 2019059412 A1 known) (CAS1207977-87-4); 3-bromo-1-(3-chloro-2-pyridyl)-N-[4,6-dichloro-3-fluoro-2-[(methylamino)carbonyl]phenyl]-1H-pyrazole-5-carboxamide (Fluchlorodiamide; known from CN110835330 A, CN106977494 A) (CAS: 2129147-03-9).

[0236] Examples of nematicides that can be mixed with the compounds and compositions of the present invention are:

[0237] (Group N-1) acetylcholinesterase (AChE) inhibitors, preferably (N-1A) carbamates selected from aldicarb, benfuracarb, carbofuran, carbofuran and thiodicarb, or (N-1B) organophosphates selected from cadusafos, ethoprofos, fenamiphos, fosthiazate, cypermethrin, phorate and terbufos.

[0238] (Group N-2) Glutamate-gated chloride channel (GluCl) allosteric modulators, preferably avermectins selected from the group consisting of abamectin and avermectin benzoate.

[0239] (Group N-3) Mitochondrial complex II electron transport inhibitors, in particular succinate-CoA reductase inhibitors, preferably selected from the pyridylmethylbenzamides of fluopyram.

[0240] (Group N-4) Lipid synthesis / growth regulation regulators, in particular acetyl-CoA carboxylase inhibitors, preferably selected from tetronic acid derivatives and tetramic acid derivatives of spirotetramat.

[0241] (Group N-UN) Compounds of various chemical nature with unknown or undefined mode of action selected from fluthiazolin, triflumizone, furfural, iprodione and tioxazafen.

[0242] (Group N-UNX) Compounds of unknown or uncertain mode of action: putative multi-site inhibitors, preferably volatile sulfur generators selected from carbon disulfide and dimethyl disulfide (DMDS), or carbon disulfide liberators selected from sodium tetrathiocarbonate, or alkyl halides selected from methyl bromide and methyl iodide (methyl iodide), or halogenated hydrocarbons selected from 1,2-dibromo-3-chloropropane (DBCP) and 1,3-dichloropropene, or chloropicrin, or methyl isothiocyanate generators selected from allyl isothiocyanate, dazomet, metampotassium and metampotassium sodium.

[0243] (Group N-UNB) Bacterial agents of unknown or undefined mode of action (non-Bt), preferably selected from the group consisting of Burkholderia spp., such as rinojensis A396; Bacillus spp., such as Bacillus firmus, Bacillus licheniformis, Bacillus amyloliquefaciens or Bacillus subtilis; Pasteuria spp., such as Pasteuria penetrans or Pasteuria nishizawae; Pseudomonas spp., such as Pseudomonas chlororaphis or Pseudomonas fluorescens; and Streptomyces spp. spp.), such as Streptomyces lydicus, Streptomyces dicklowii or Streptomyces albogriseolus.

[0244] (Group N-UNF) Fungal agents with unknown or undefined mode of action, preferably selected from the group consisting of the following fungi or fungal derivatives: Actinomyces spp., for example Actinomyces streptococcus; Arthrobotrys spp., for example Arthrobotrys oligospora; Aspergillus spp., for example Aspergillus niger; Muscodor spp., for example Muscodor albus; Myrothecium spp., for example Myrothecium verrucaria; Paecilomyces spp., for example Paecilomyces lilacinus; lilacinum), Paecilomyces carneus, or Paecilomyces fumosoroseus; Pochonia spp., such as Pochonia chlamydosporia; and Trichoderma spp., such as Trichoderma harzianum, Trichoderma virens, Trichoderma atroviride, or Trichoderma viride.

[0245] (Group N-UNE) Preparations of plant or animal origin of unknown or undefined mode of action, including synthetic extracts and unrefined oils, preferably selected from the group consisting of azadirachtin, camellia seed cake, essential oils, garlic extract, pongamia oil, terpenes such as carvacrol and Quillaja saponaria extract.

[0246] Examples of herbicides that can be mixed with the compounds and compositions of the present invention are:

[0247] Acetochlor, acifluorfen, acifluorfen-methyl, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, Aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, aminopyralid-dimethylammonium, aminopyralid-tripromine, amitrole, ammoniumsulfamate, anilofos, asulam, asulam-potassium, asulam sodium sodium), atrazine, azafenidin, azimsulfuron, beflubutamid, (S)-(-)-beflubutamid, beflubutamid-M, benazolin, benazolin-ethyl, benazolin-dimethylammonium, benazolin-potassium, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, bentazone-sodium, benzobicyclon, benzofenap, bicyclopyrone, bifenox,Bialafos, bilanafos-sodium, bipyrazone, bispyribac, bispyribac-sodium, bixlozone, bromacil, bromacil-lithium, bromacil-sodium, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyryl rate), bromoxynil-potassium, bromoxynil-heptanoate and bromoxynil-octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, cambendic hlor), carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chloramben-ammonium, chloramben-diolamine, chlroamben-methyl, chloramben-methylammonium, chloramben-sodium, chlorbromuron, chlorfenac, chlorfenac-ammonium, chlorfenac-sodium, chlorfenprop, chlorfenprop-methyl, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron,Chlorsulfuron, chlorthal, chlorthal-dimethyl, chlorthal-monomethyl, cinidon, cinidon-ethyl, cinmethylin, exo-(+)-cinmethylin (i.e. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane), exo-(-)-cinmethylin (i.e. (1R,2S,4S)-4-isopropyl-1-methyl-2-[( 2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane), cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-ethyl, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-methyl, clopyralid-olamine, Clopyralid-potassium, clopyralid-tripomine, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl cyhalofop-butyl), cyprazine, 2,4-D (including its salts: 2,4-D-ammonium, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-choline, 2,4-D-diethylammonium, 2,4-D-dimethylammonium, 2,4-D-diethanolamine, 2,4-D-doboxyl, 2,4-D-dodecylammonium, 2,4-D-ethylhexyl, 2,4-D-etexyl, 2,4-D-ethyl, 2,4-D-2-ethylhexyl,2,4-D-heptyl ammonium, 2,4-D-isobutyl ester, 2,4-D-isooctyl ester, 2,4-D-isopropyl ester, 2,4-D-isopropyl ammonium, 2,4-D-lithium, 2,4-D-methylheptyl ester (2,4-D-meptyl), 2,4-D-methyl ester, 2,4-D-potassium, 2,4-D-tetradecyl ammonium, 2,4-D-triethylammonium, 2,4-D-triisopropanolammonium, 2,4-D-tripropylamine (2,4-D-tripromine) and 2,4-D-trolamine), 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isooctyl, 2,4-DB-potassium and 2,4-DB-sodium, daimuron (dymron), dalapon, dalapon-calcium, dalapon-magnesium sium), dalapon-sodium, dazomet, dazomet-sodium, n-decyl alcohol, 7-deoxy-D-sedoheptulose, desmedipham, detosyl-pyrazolate (DTP), dicamba and its salts (e.g., dicamba-biproamine, dicamba-N,N-bis(3-aminopropyl)methylamine, dicamba-butotyl, dicamba-choline, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diethanolamine ammonium (dicamba-diethanolamine ammonium), dicamba-diethylammonium, dicamba-isopropylammonium, dicamba-methyl ester, dicamba-monoethanolamine, dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-triethanolamine), dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-butotyl,2,4-dichlorprop-dimethylammonium, dichlorprop-etexyl, dichlorprop-ethylammonium, dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-potassium, dichlorprop-sodium, dichlorprop-dimethylammonium, dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-potassium, dichlorprop-sodium, dichlorprop-dimethylammonium, dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-isoctyl ... rprop-P), dichlorprop-P-dimethylammonium, dichlorprop-P-etexyl, dichlorprop-P-potassium, dichlorprop-sodium, diclofop, diclofop-methyl, diclofop-P, diclofop-P-methyl, diclosulam, wild swallow difenzoquat, difenzoquat-metilsulfate, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimesulfazet, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethachlor dimetrasulfuron), diinitramine, dinoterb, dinoterb-acetate, diphenamid, diquat, diquat-dibromid, diquat-dichloride, dithiopyr, diuron, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium,Endothal, endothal-diammonium, endothal-dipotassium, endothal-disodium, Epyrifenacil (S-3100), EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, chlorfluralin Ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-5231 (i.e., N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]-ethanesulfonamide), F-7967 (i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione), fenoxaprop, fenoxaprop -P), fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, flamprop, flamprop-isoproyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, pyridine flazasulfuron, florasulam, florpyrauxifen, florpyrauxifen-benzyl, fluazifop, fluazifop-butyl, fluazifop-methyl, fluazifop-P, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium,flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, flurenol-dimethylammonium and flurenol-methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, sodium tetrafluoropropionate, flu propanate-sdium), flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, foramsulfuron sodium sodium salt), fosamine, fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-sodium, L-glufosinate-ammonium, L-glufosinate-sodium, glufosinate-P-sodium, glufosinate-P-ammonium, glyphosate, glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-diammonium,glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-sesquisodium, glyphosate-trimesium, H-9201 (O-(2,4-dimethyl-6-nitrophenyl)-O-ethyl-isopropylphosphoramidothioate) ioat), halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-methyl, haloxyfop-methyl aloxyfop-P-methyl), haloxifop-sodium, hexazinone, HNPC-A8169 (i.e. (2S)-2-{3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy}propionic acid prop-2-yn-1-yl ester), HW-02 (i.e. 1-(dimethoxyphosphoryl)-ethyl-(2,4-dichlorophenoxy)acetate), hydantocidin, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium 、imazapic、imazapic-ammonium、imazapyr、imazapyr-isopropylammonium、imazaquin、imazaquin-ammonium、imazaquin.methyl、imazethapyr、imazethapyr-immonium、imazosulfuron、indanofan、indaziflam, iodosulfuron, iodosulfuron-methyl, iodosulfuron-methyl-sodium, ioxynil, ioxynil-lithium, ioxynil-octanoate, ioxynil-potassium and ioxynil-sodium, ipfencarbazone, isoproturon, isoxazolidinone uron), isoxaben, isoxaflutole, karbutilate, KUH-043 (i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole), ketospiradox, ketospiradox-potassium, lactofen, lancotrione, lenacil, linuron, MCPA, MCPA-butoxyethyl ester, MCPA-butyl ester, MCPA-dimethylammonium, MCPA-diethanolamine (MCPA-diolamine), MCPA-2-ethylhexyl ester, MCPA-ethyl ester, MCPA-isobutyl ester, MCPA-isooctyl ester, MCPA-isopropyl ester, MCPA-isopropylammonium, MCPA-methyl ester, MCPA-ethanolamine (MCPA-olamine), MCPA-potassium, MCPA-sodium and MCPA-triethanolamine (MCPA-trolamine), MCPB, MCPB-methyl ester, MCPB-ethyl ester and MCPB-sodium, 2-methyl-4-chloropropionic acid (mecoprop), 2-methyl-4-chloropropionic acid butoxyethyl ester (mecoprop-butotyl), 2 - dimethylammonium methyl-4-chloropropionate, mecoprop-diolamine, mecoprop-etexyl, mecoprop-ethadyl, mecoprop-isooctyl, methyl methyl-4-chloropropionate, potassium methyl-4-chloropropionate, sodium methyl-4-chloropropionate and triethanolamine methyl-4-chloropropionate, mecoprop-P, mecoprop-P-butotyl,2-Methyl-4-chloropropionic acid-dimethylammonium ester, 2-ethylhexyl 2-methyl-4-chloropropionic acid ester and 2-methyl-4-chloropropionic acid potassium ester, mefenacet, mefluidide, mefluidide-diolamine, mefluidide-potassium, mesosulfuron, mesosulfuron-methyl, mesosulfuron sodium, mesotrione, methabenzthiazuron, mefenacet tam), metamifop, metamitron, metazachlor, metazosulfuron, methylbenzimidazole, methiopyrsulfuron, metiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl tsulfuron), metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron-methyl, MT-5950 (i.e. N-[3-chloro-4-(1-methylethyl)-phenyl]-2-methylpentanamide), NGGC-011, napropamide, NC-310 (i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole), NC-656 (i.e. 3-[(isopropylsulfonyl)methyl]-N-(5-methyl-1,3 ,4-oxadiazol-2-yl)-5-(trifluoromethyl)[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide), neburon, nicosulfuron, pelargonic acid, norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon,Oxyfluorfen, paraquat, paraquat dichloride, paraquat-dimethylsulfate, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, mineral oil, phenmedipham, phenmedipham-ethyl, picloram, picloram dimethylammonium, ammonia chloride picloram-etexyl, 2-ethylhexyl picloram, methyl picloram, ethanolamine picloram, potassium picloram, triethylammonium picloram, tripropylamine picloram, triethanolamine picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, Primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium um), propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl,pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, dimethyl quinclorac ammonium, methyl quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl ), QYM201 (i.e., 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin-2-one), rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron- methyl), sulfosulfuron, SYP-249 (i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl-5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate), SYP-300 (i.e., 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione), 2,3,6-TBA, TCA (trichloroacetic acid) and its salts (e.g., TCA-ammonium, TCA-calcium, TCA-ethyl, TCA-magnesium, TCA-sodium), tebuthiuron,tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, tetflupyrolimet, thaxtomin, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone hiencarbazone-methyl), thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, bensulfuron-methyl ribenuron), tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-choline, triclopyr ethyl, triclopyr triethylammonium, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifloxacin fluralin), triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862 (i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline), 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid ethyl ester,ethyl-[(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetate, 3-chloro-2-[3-(difluoromethyl)isoxazolyl-5-yl]phenyl-5-chloropyrimidin-2-yl ether, 2-(3,4-dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-6-methylpyridazin-3(2H)-one, 2-({2-[(2-methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexane-1,3-dione, (5-hydroxy-1-methyl-1H-pyrazol-4-yl) ( 3,3,4-trimethyl-1,1-dioxo-2,3-dihydro-1-benzothiophen-5-yl)methanone, 1-methyl-4-[(3,3,4-trimethyl-1,1-dioxo-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazol-5-ylpropane-1-sulfonate, 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1-methyl-1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazole-4-carboxylate, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid cyanomethyl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid prop-2-yn-1-yl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid methyl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid benzyl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid ethyl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1-isobutyryl-1H-indol-6-yl ) pyridine-2-carboxylic acid methyl ester, 6-(1-acetyl-7-fluoro-1H-indol-6-yl)-4-amino-3-chloro-5-fluoropyridine-2-carboxylic acid methyl ester, 4-amino-3-chloro-6-[1-(2,2-dimethylpropionyl)-7-fluoro-1H-indol-6-yl]-5-fluoropyridine-2-carboxylic acid methyl ester, 4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indol-6-yl]pyridine-2-carboxylic acid methyl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid potassium, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid sodium4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) pyridine-2-carboxylic acid butyl ester, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 3-(5-tert-butyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolidin-2-one, 3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolidin-2-one, 4-hydroxy-1-methoxy-5-methyl- 3-[4-(Trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione, 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1-methylquinazoline-2,4(1H,3H)-dione, 2-[2-chloro-4-(methylsulfonyl)- [3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex-2-en-1-one, 1-(2-carboxyethyl)-4-(pyrimidin-2-yl)pyridazin-1-ium salt (having an anion such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(pyridazin-3-yl)pyridazin-1-ium salt (having an anion such as chloride, acetate or trifluoroacetate), 4-(pyrimidin-2-yl)-1-(2-sulfoethyl)pyridazin-1-ium salt (having an anion such as chloride, acetate or trifluoroacetate), , acetate or trifluoroacetate), 4-(pyridazin-3-yl)-1-(2-sulfoethyl)pyridazin-1-ium salt (having an anion such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3-thiazol-2-yl)pyridazin-1-ium salt (having an anion such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3-thiazol-2-yl)pyridazin-1-ium salt (having an anion such as chloride, acetate or trifluoroacetate).

[0248] Examples of plant growth regulators that can be admixed with the compounds and compositions of the present invention are:

[0249] Abscisic acid and related analogs [e.g., (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate, methyl-(2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate, (2Z,4E)-3-ethyl-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-dienoate, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-dienoate, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoic acid methyl ester, (2Z,4E)-5-(2-hydroxy-1,3-dimethyl-5-oxobicyclo[4.1.0]hept-3-en-2-yl)-3-methylpenta-2,4-dienoic acid], activated ester (acibenzolar), benzothiadiazole (acibenzolar-S-methyl), S-adenosylhomocysteine ​​(S-adenosylhomocysteine) ocysteine), allantoin, 2-aminoethoxyvinylglycine (AVG), aminooxyacetic acid and related esters [e.g. (isopropylidene)-aminooxyacetic acid-2-(methoxy)-2-oxoethyl ester, (isopropylidene)-aminooxyacetic acid-2-(hexyloxy)-2-oxoethyl ester, (cyclohexylidene)-aminooxyacetic acid-2-(isopropoxy)-2-oxoethyl ester], 1-aminocyclopropane-1-ylcarboxylic acid and its derivatives (e.g. disclosed in DE3335514, EP30287, DE2906507 or US5123951), 5-aminolevulinic acid, pyrimidine alcohol (ancy midol), 6-benzylaminopurine, bikinin, brassinolide, brassinolide-ethyl, L-canaline, catechin, and catechins (e.g., (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromen-3,5,7-triol).7-triol)), chitooligosaccharides (CO; CO differs from LCO in that it lacks the fatty acid side chains that are characteristic of LCO. CO (sometimes called N-acetyl chitooligosaccharides) also contain GlcNAc residues, but have side chain modifications that distinguish them from chitin molecules [(C8H13NO5)n, CAS No. 1398-61-4] and chitosan molecules [(C5H11NO4)n, CAS No. 9012-76-4]), chitin compounds, chlormequat chloride), cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, 1-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-[2-(4-cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, daminozide, dazomet, dazomet sodium, n-decanol, dikegulac, dikegulac-sodium, endoxan, endoxan dipotassium, endoxan disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flufenamide, fluorenol butyl ester, fluorenol methyl ester, flurprimidol, forchlorfenuron, gibberellic acid acid), inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid or its derivatives (e.g., methyl jasmonate, ethyl jasmonate), lipo-chitooligosaccharide (LCO, sometimes referred to as symbiotic nodulation (Nod) signal (or Nod factor) or Myc factor, composed of β-l, N-linked fatty acyl chains condensed at the non-reducing end,4-linked N-acetyl-D-glucosamine ("GlcNAc") residues. As is understood in the art, LCOs differ in the number of GlcNAc residues in the backbone, the length and degree of saturation of the fatty acyl chains, and the substitution of reducing and non-reducing sugar residues), linoleic acid or its derivatives, linolenic acid or its derivatives, maleic hydrazide, mepiquat chloride, mepiquat pentaborate, pentaborate), 1-methylcyclopropene, 3-methylcyclopropene, 1-ethylcyclopropene, 1-n-propylcyclopropene, 1-cyclopropenylmethanol, methoxyvinylglycine (MVG), 3'-methylabscisic acid, 1-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinolin-6-yl)methylsulfonamide and related substituted tetrahydroquinolin-6-yl)methylsulfonamides, (3E,3aR,8bS)-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylene)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b] furan-2-one and related lactones as summarized in EP2248421, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, 4-phenylbutyric acid and its salts (e.g. sodium 4-phenylbutyrate, potassium 4-phenylbutyrate), phenylalanine, N-phenylphthalic acid, prohexadione, prohexadione-calcium, putrescine, prohydrojasmon, rhizobitoxin, salicylic acid, methyl salicylate, sarcosine, sine), sodium cycloprop-1-en-1-yl acetate, sodium cycloprop-2-en-1-yl acetate, sodium 3-(cycloprop-2-en-1-yl) propionate, sodium 3-(cycloprop-1-en-1-yl) propionate, sidefungin, spermidine, spermine, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tryptophan, tsitodef, uniconazole, uniconazole-P, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine.

[0250] Examples of safeners that can be admixed with the compounds and compositions of the invention are:

[0251] S1) A compound selected from the class of heterocyclic carboxylic acid derivatives:

[0252] S1 a ) dichlorophenylpyrazoline-3-carboxylic acid compounds (S1 a ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) ("mefenpyr-diethyl"), and related compounds as described in WO-A-91 / 07874;

[0253] S1 b )Dichlorophenylpyrazolecarboxylic acid derivatives (S1b ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylic acid ethyl ester (S1-2), 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylic acid ethyl ester (S1-3), 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylic acid ethyl ester (S1-4), and related compounds as described in EP-A-333131 131 and EP-A-269806;

[0254] S1 c )1,5-diphenylpyrazole-3-carboxylic acid derivatives (S1 c ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester (S1-5), 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylic acid methyl ester (S1-6), and related compounds as described in, for example, EP-A-268554;

[0255] S1 d )Triazole carboxylic acid compounds (S1 d ), preferably compounds such as fenchlorazole (ethyl ester), i.e. 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester (S1-7), and related compounds as described in EP-A-174562 and EP-A-346620;

[0256] S1 e )5-benzyl-2-isoxazoline-3-carboxylic acid or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid compounds (S1 e ), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9), and related compounds as described in WO-A-91 / 08202, or 5,5-diphenyl-2-isoxazolinecarboxylic acid (S1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) ("isoxadifen-ethyl") or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13), as described in patent application WO-A-95 / 07897.

[0257] S2) A compound selected from the group consisting of 8-quinolinyloxy derivatives (S2):

[0258] S2 a)8-quinolinyloxyacetic acid compounds (S2 a ), preferably (5-chloro-8-quinolinyloxy)acetic acid 1-methylhexyl ester ("cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinyloxy)acetic acid 1,3-dimethylbutyl-1-yl ester (S2-2), (5-chloro-8-quinolinyloxy)acetic acid 4-allyloxybutyl ester (S2-3), (5-chloro-8-quinolinyloxy)acetic acid 1-allyloxyprop-2-yl ester (S2-4), (5-chloro-8-quinolinyloxy)acetic acid 1,3-dimethylbutyl-1-yl ester (S2-5), (5-chloro-8-quinolinyloxy)acetic acid 1,3-dimethylbutyl-1-yl ester (S2-6), (5-chloro-8-quinolinyloxy)acetic acid 1,3-dimethylbutyl-1-yl ester (S2-7), (5-chloro-8-quinolinyloxy)acetic acid 1,3-dimethylbutyl-1-yl ester (S2-8), (5-chloro-8-quinolinyloxy)acetic acid 1,3-dimethylbutyl-1-yl ester (S2-9), (5-chloro-8-quinolinyloxy)acetic acid 1,3-dimethylbutyl-1-yl ester (S2-10), (5-chloro-8-quinolinyloxy)acetic acid 1,3-dimethylbutyl-1-yl ester (S2-11), (5-chloro-8-quinolinyloxy)acetic acid 1,3-dimethylbutyl-1-yl ester (S2-12), (5-chloro-8-quinolinyloxy)acetic acid 1,3-dimethylbutyl-1-yl ester (S2-13), (5-chloro-8-quinolinyloxy)acetic acid 1,3-dimethylbutyl-1-yl ester (S2-14), (5-chloro-8-quinolinyloxy) ethyl ester (S2-5), 5-chloro-8-quinolinyloxyacetic acid methyl ester (S2-6), (5-chloro-8-quinolinyloxy)acetic acid allyl ester (S2-7), (5-chloro-8-quinolinyloxy)acetic acid 2-(2-propyleneiminooxy)-1-ethyl ester (S2-8), (5-chloro-8-quinolinyloxy)acetic acid 2-oxopropan-1-yl ester (S2-9), and as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 Related compounds described in 492 366, and (5-chloro-8-quinolinyloxy)acetic acid (S2-10), its hydrates and salts thereof, such as its lithium salt, sodium salt, potassium salt, calcium salt, magnesium salt, aluminum salt, iron salt, ammonium salt, quaternary ammonium salt, sulfonium salt or phosphonium salt, as described in WO-A-2002 / 34048;

[0259] S2 b (5-chloro-8-quinolinyloxy)malonic acid compounds (S2 b ), preferably compounds such as diethyl (5-chloro-8-quinolyloxy)malonate, diallyl (5-chloro-8-quinolyloxy)malonate, methyl ethyl (5-chloro-8-quinolyloxy)malonate and related compounds as described in EP-A-0 582 198.

[0260] S3) Active compounds of the dichloroacetamide class (S3), which are usually used as pre-emergence safeners (safeners acting on the soil), for example "dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) (S3-2) from Stauffer, "R-28725" (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) (S3-3) from Stauffer, "benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4) from PPG Industries, “PPG-1292” (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) (S3-5), Sagro-Chem, “DKA-24” (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) (S3-6), Nitrokemia or Monsanto, “AD-67” or “MON 4660” (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) (S3-7), TRI-Chemical "TI-35" (1-dichloroacetylazepane) (S3-8) from RT, "Diclonon" (Dicyclonon) or "BAS145138" or "LAB145138" (S3-9) ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) purchased from BASF, "furilazole" or "MON 13900" ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10), and its (R) isomer (S3-11).

[0261] S4) A compound selected from the group consisting of acylsulfonamides (S4):

[0262] S4 a ) N-acylsulfonamides and salts thereof, as described in WO-A-97 / 45016,

[0263] S4 b )4-(benzoylsulfamoyl)benzamide compounds and salts thereof, as described in WO-A-99 / 16744,

[0264] S4 c) compounds of the benzoylsulfamoylphenyl urea class, as described in EP-A-365484, for example, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea and 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea;

[0265] S4 d ) Compounds of the N-phenylsulfonylterephthalamide class and their salts, which are known, for example, from CN 101838227.

[0266] S5) Active compounds (S5) selected from the group consisting of hydroxyaromatic compounds and aromatic-aliphatic carboxylic acid derivatives, for example ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004 / 084631, WO-A-2005 / 015994, WO-A-2005 / 016001.

[0267] S6) An active compound (S6) selected from the group consisting of 1,2-dihydroquinoxaline-2-ones, for example 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxaline-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxaline-2-one, as described in WO-A-2005 / 112630.

[0268] S7) A compound (S7) selected from the class of diphenylmethoxyacetic acid derivatives, such as methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid, as described in WO-A-98 / 38856.

[0269] S8) 2-Fluoroacrylic acid derivatives as described in WO-A-98 / 27049.

[0270] S9) an active compound (S9) selected from the group consisting of 3-(5-tetrazolylcarbonyl)-2-quinolones, for example 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-199 / 000020;

[0271] S10) N-acylsulfonamides as described in WO-A-2007 / 023719 and WO-A-2007 / 023764.

[0272] S11) Active compounds from the class of the oxyimino compounds (S11), which are known as seed dressings, for example

[0273] "oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed dressing safener for millet / sorghum against metolachlor damage,

[0274] "fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is known as a seed dressing safener for millet / sorghum against metolachlor damage, and

[0275] "Cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed dressing safener for millet / sorghum against metolachlor damage.

[0276] S12) is an active compound (S12) selected from the class of isothiochromanone, for example [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetic acid methyl ester (CAS Reg. No. 205121-04-6) (S12-1), and related compounds from WO-A-1998 / 13361.

[0277] S13) one or more compounds from group (S13):

[0278] "Naphthalic anhydride" (1,8-naphthalene dicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for corn against damage by thiocarbamate herbicides,

[0279] "fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice,

[0280] "flurazole" (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), known as a seed dressing safener for millet / sorghum against alachlor and isopropylamine damage,

[0281] "CL 304415" (CAS Reg. No. 31541-57-8) purchased from American Cyanamid

[0282] (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4), which is known as a safener for corn against damage by imidazolinones,

[0283] "MG 191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn,

[0284] "MG 838" from Nitrokemia (CAS Reg. No. 133993-74-5) (2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6),

[0285] "disulfoton" (S-2-ethylthioethyl dithiophosphoric acid O,O-diethyl ester) (S13-7),

[0286] "Dietholate" (O-phenylthiophosphorothioate O,O-diethyl ester) (S13-8),

[0287] "mephenate" (4-chlorophenyl methylcarbamate) (S13-9).

[0288] S14) Active compounds which, in addition to their herbicidal action on weeds, also act as safeners for crop plants (such as rice), e.g.

[0289] "Piperidin" or "MY-93" (S-1-methyl 1-phenylethylpiperidin-1-carbothioate), which is known as a safener for rice against damage by the herbicide graminete,

[0290] "Methiocarb" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as a safener for rice against damage by the herbicide pyrazosulfuron-methyl,

[0291] "benzyluron" = "JC-940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087254), which is known as a safener for rice against damage by some herbicides,

[0292] "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against damage by some herbicides,

[0293] "CSB" (1-bromo-4-(chloromethylsulfonyl)benzene), (CAS Reg. No. 54091-06-4), available from Kumiai, is known as a safener for use in rice against damage by some herbicides.

[0294] S15) Pyridine-2-oxy-benzamides as described in WO-A-2008 / 131861 and WO-A-2008 / 131860.

[0295] S16) Active compounds which are mainly used as herbicides but also have a safener effect on crop plants, for example (2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (2-methyl-4-chloropropionic acid), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 3,6-dichloro-2-methoxybenzoic acid 1-(ethoxycarbonyl)ethyl ester (lactidichlor-ethyl).

[0296] Examples of nitration inhibitors that can be mixed with the compounds and compositions of the present invention are selected from the group consisting of 2-(3,4-dimethyl-1H-pyrazol-1-yl)succinic acid, 2-(4,5-dimethyl-1H-pyrazol-1-yl)succinic acid, 3,4-dimethyl pyrazolium glycolate, 3,4-dimethyl pyrazolium citrate, 3,4-dimethyl pyrazolium lactate, 3,4-dimethyl pyrazolium mandelate, 1,2,4-triazole, 4-chloro-3-methylpyrazole, N-((3(5)-methyl-1H-pyrazol-1-yl)methyl)acetamide, N-((3 1-((2-cyanoguanidine)methyl)urea, 2-cyano-1-((2-cyanoguanidine)methyl)guanidine, 2-chloro-1-((4-chloro-3(5)-methyl-1H-pyrazol-1-yl)methyl)formamide; reaction adducts of dicyandiamide, urea and formaldehyde, triazolyl-formaldehyde-dicyandiamide adduct, 2-cyano-1-((4-oxo-1,3,5-triazinane (azinan)-1-yl)methyl)guanidine, 1-((2-cyanoguanidine)methyl)urea, 2-cyano-1-((2-cyanoguanidine)methyl)guanidine, 2-chloro -6-(Trichloromethyl)-pyridine (nitrapyrin or N-serve), dicyandiamide, 3,4-dimethylpyrazole phosphate, 4,5-dimethylpyrazole phosphate, 3,4-dimethylpyrazole, 4,5-dimethylpyrazole, ammonium thiosulfate, neem, products based on neem, linoleic acid, alpha-linolenic acid, p-coumaric acid methyl ester, ferulate methyl ester, 3-(4-hydroxyphenyl) propionate methyl ester, hyoscyamine, brachialacton, p-benzoquinone sorgoleone, 4-amino-1,2, 4-Triazole hydrochloride, 1-amino-2-thiourea, 2-amino-4-chloro-6-methylpyrimidine, 2-mercapto-benzothiazole, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole (terrazole, etridiazole), 2-sulfanilamidothiazole, 3-methylpyrazole, 1,2,4-triazolethiourea, cyanamide, melamine, zeolite powder, catechol, benzoquinone, sodium tetraborate, allylthiourea, chlorate and zinc sulfate.

[0297] The compounds and compositions of the present invention may be combined with one or more agriculturally beneficial agents.

[0298] Examples of agriculturally beneficial agents include: biostimulants, plant growth regulators, plant signaling molecules, growth promoters, microbial stimulatory molecules, biomolecules, soil conditioners, nutrients, plant nutrition enhancers, and the like, such as lipo-chitooligosaccharides (LCO), chitooligosaccharides (CO), chitin compounds, flavonoids, jasmonic acid or its derivatives (e.g., jasmonates), cytokinins, plant growth hormones, gibberellins, abscisic acid, ethylene, brassinolide, salicylates, macro- and micronutrients, linoleic acid or its derivatives, linolenic acid or its derivatives, karrikins, and beneficial microorganisms (e.g., Rhizobium spp., Bradyrhizobium spp., Sinorhizobium spp., Azorhizobium spp., Glomus spp., Giant Sporangium spp., Hymenoscyphous spp., Oidiodendron spp., Laminaria spp., Pisolithus spp. spp.), Psoralea, Scleroderma, Rhizoctonia, Acinetobacter, Arthrobacter, Arthrobotrys, Aspergillus, Azospirillum, Bacillus, Burkholderia, Candida, Chryseomonas, Enterobacter, Eupenicillium, Exiguobacterium, Klebsiella, Kluyvera, Microbacterium, Mucor, spp.), Paecilomyces spp., Paenibacillus spp., Penicillium spp., Pseudomonas spp., Serratia spp., Stenotrophomonas spp., Streptomyces spp., Swaminathania spp., Thiobacillus spp., Torulospora spp., Vibrio spp., Xanthobacter spp.), Xanthomonas spp., etc.), and combinations thereof.

[0299] According to certain embodiments, the compounds and compositions of the present invention may be used in combination with one or more biostimulants. Biostimulants may enhance metabolic or physiological processes such as respiration, photosynthesis, nucleic acid absorption, ion absorption, nutrient transport, or a combination thereof. Non-limiting examples of biostimulants that may be included or used in the compositions of the present invention may include seaweed extracts (e.g., ascophyllum nodosum; BAYFOLAN ALGAE, Aglukon gmbH, Germany), bacterial extracts (e.g., extracts of one or more nitrogen-fixing bacteria, phosphate-dissolving microorganisms and / or biopesticides), fungal extracts, humic acid (e.g., potassium humate), fulvic acid, inositol and / or glycine, protein hydrolysates and amino acids from animals, such as potassium humate), fulvic acid, inositol and / or glycine, hydrolyzed proteins and amino acids (including animal sources BAYFOLAN AMBITION & BAYFOLAN cobre, SICIT, Italy) and plant sources, inorganic compounds (such as silica), and any combination thereof. According to certain embodiments, the biostimulant may include one or more Azospirillum extracts (e.g., extracts of a medium comprising Azospirillum brasiliensis INTA Az-39), one or more Bradyrhizobium species extracts (e.g., extracts of a medium comprising B. elkanii SEMIA 501, B. elkanii SEMIA 587, B. elkanii SEMIA 5019, B. japonicum NRRL B-50586 (also as NRRL B-59565), B. japonicum NRRL B-50587 (also as NRRL B-59566), B. japonicum NRRL B-50588 (also as NRRL B-59567), B. japonicum NRRL B-50589 (also as NRRL B-59568), B. japonicum NRRL B-50590 (also as NRRL B-59569), B. japonicum NRRL B-50591 (also as NRRL B-59570), B. japonicum NRRL B-50592 (also as NRRL B-59571), B. japonicum NRRL B-50593 (also as NRRL B-59572), B. japonicum NRRL B-50594 (also as NRRL B-50493), B. japonicum NRRL B-50608, B. japonicum NRRL B-50609, B. japonicum NRRL B-50610, B. japonicum NRRL B-50611, B.japonicum NRRL B-50612, B.japonicum NRRL B-50726, B.japonicum NRRL B-50727, B.japonicum NRRL B-50728, B.japonicum NRRL B-50729, B.japonicum NRRL B-50730, B.japonicum SEMIA 566, B.japonicum SEMIA 5079, B.japonicum SEMIA 5080, B.japonicum USDA 6, B.japonicum USDA 110, B.japonicum USDA 122, B.japonicum USDA123, B.japonicum USDA 127, B.japonicum USDA129 and / or B.japonicum USDA 532C), one or more Rhizobium extracts (e.g., the extracts of the medium include R. leguminosarum SO12A-2), one or more Sinorhizobium meliloti extracts (e.g., the extracts of the medium include S. fredii CCBAU114 and / or S. fredii USDA205), one or more Penicillium extracts (e.g., the extracts of the medium include P. bilaiae ATCC 18309, P. bilaiae ATCC 20851, P. bilaiae ATCC 22348, P. bilaiae NRRL 50162, P. bilaiae NRRL50169, P. bilaiae NRRL 50776, P. bilaiae NRRL 50777, P. bilaiae NRRL 50778, P. bilaiae NRRL 50777, P. bilaiae NRRL 50778, P. bilaiae NRRL 50779, P.bilaiae NRRL50780, P.bilaiae NRRL 50781, P.bilaiae NRRL 50782, P.bilaiae NRRL 50783, P.bilaiae NRRL 50784, P.bilaiae NRRL 50785, P.bilaiae NRRL 50786, P.bilaiae NRRL50787, P.bilaiae NRRL 50788, P.bilaiae RS7B-SD1, P.brevicompactum AgRF18, P.canescens ATCC 10419, P.expansum ATCC 24692, P. expansum YT02, P. fellatanum ATCC 48694, P. gaestrivorus NRRL 50170, P. glabrum DAOM 239074, P. glabrum CBS 229.28, P. janthinellum ATCC 10455, P. lanocoeruleum ATCC 48919, P. radicum ATCC 201836, P. radicum FRR 4717, P. radicum FRR 4719, P. radicum N93 / 47267 and / or P. raistrickii ATCC 10490), one or more Pseudomonas extracts (e.g., extracts of P. jessenii in a medium comprising PS06), one or more acaricidal, insecticidal and / or nematicidal extracts (e.g., extracts of the medium include Bacillus firmus I-1582, Bacillus mycoides AQ726, NRRL B-21664; Beauveria bassiana ATCC-74040, Beauveria bassiana ATCC-74250, Burkholderia sp. A396 sp. nov. rinojensis, NRRL B-50319, Chromobacterium spp. NRRL B-30655, Chromobacterium vaccinii NRRL B-50880, Flavobacterium H492, NRRL B-50584, Metarhizium anisopliae F52 (also known as Metarhizium anisopliae strain 52, Metarhizium anisopliae strain 7, Metarhizium anisopliae strain 43 and Metarhizium anisopliae BIO-1020, TAE-001; as DSM 3884, DSM 3885, ATCC 90448, SD 170 and ARSEF 7711) and / or Paecilomyces fumosorum FE991), and / or one or more fungal extracts (e.g., extracts of a medium including Parasitium graminis AQ. (Intrachem Bio GmbH & Co. KG, Germany), Aspergillus flavus (Syngenta Crop Protection, Inc., CH), Aureobasidium (bio ferm GmbH, Germany), Bacillus pumilus AQ717 (NRRL B21662), Bacillus pumilus NRRL B-30087, Bacillus AQ175 (ATCC 55608), Bacillus AQ177 (ATCC 55609), Bacillus subtilis AQ713 (NRRL B-21661), Bacillus subtilis AQ743 (NRRL B-21665), Bacillus subtilis var. amyloliquefaciens FZB24, Bacillus subtilis var. amyloliquefaciens NRRL B 50349, Bacillus subtilis var. amyloliquefaciens TJ1000 (also known as 1BE, isolate ATCC BAA-390), Bacillus thuringiensis AQ52 (NRRL B-21619), Candida oleophila I 82 (e.g., Purchased from Ecogen Inc., USA), Candida saitoana (mixed with lysozyme; BASF, USA) and (Arysta LifeScience, Ltd., Cary, NC), Gliocladium schrenkiana J1446 ( Verdera, Finland), (Prophyta, Germany), Cryphonectria parasitica (CNICM, France), Cryptococcus albidus YIELD (Anchor BioTechnologies, South Africa), Fusarium oxysporum (purchased from SIAPA, Italy) and (Natural Plant Protection, France), Drupe Saccharomyces cerevisiae (Agrogreen, Israel), Microdochium dimerum (Agrauxine, France), Muscodor albus NRRL 30547, Muscodor albus NRRL 30548, (Verdera, Finland), yeast Pseudomonas flocculans (Plant Products Co. Ltd., Canada), Pythium oligandrum DV74 ( Remeslo SSRO, Biopreparaty, Czech Rep.), Reynoutria sachlinensis (e.g., purchased from Marrone BioInnovations, USA), Streptomyces lydicus NRRLB-30145, Streptomyces lydicus M1064, Streptomyces galbus NRRL 30232, Streptomyces lydicus WYEC 108 (ATCC 55445), Streptomyces violaceus niger YCED 9 (ATCC 55660; and THATCH Idaho Research Foundation, USA), Streptomyces WYE 53 (ATCC 55750; and THATCH Idaho Research Foundation, USA), Xanthocyanobacterium V117b ( Prophyta, Germany), Trichoderma aspergillus SKT-1 ( Kumiai Chemical Industry Co., Ltd., Japan), Trichoderma viridis LC52 ( Agrimm Technologies Ltd, NZ), Trichoderma harzianum T 22 ( der Firma BioWorks Inc., USA), Trichoderma harzianum TH-35 (ROOT purchased from Mycontrol Ltd., Israel), Trichoderma harzianum T 39 ( Mycontrol Ltd., Israel; TRICHODERMA Makhteshim Ltd., Israel), Trichoderma harzianum ICC012 and Trichoderma viride TRICHOPEL (Agrimm Technologies Ltd, NZ), Trichoderma harzianum ICC012 and Trichoderma viride ICC080 ( WP, Isagro Ricerca, Italy), Trichoderma polysporum and Trichoderma harzianum ( BINAB Bio Innovation AB, Sweden), Trichoderma (CEPLAC, Brazil), Trichoderma virens GL 21 ( Certis LLC, USA), Trichoderma harzianum G1-3, ATCC 57678, Trichoderma harzianum G1-21 (Thermo Trilogy Corporation, Wasco, CA), Trichoderma harzianum G1-3 and Bacillus subtilis starch var. FZB2, Trichoderma harzianum G1-3 and Bacillus subtilis starch var. NRRL B50349, Trichoderma harzianum G1-3 and Bacillus subtilis starch var. TJ1000, Trichoderma harzianum G1-21 and Bacillus subtilis starch var. FZB24, Trichoderma harzianum G1-21 and Bacillus subtilis starch var. NRRL B 50349, Trichoderma harzianum G1-21 and Bacillus subtilis starch var. TJ1000, Trichoderma viride (Ecosense Labs. (India) Pvt. Ltd., Indien, F purchased from T. Stanes & Co. Ltd., India), Trichoderma viride TV1 (Agribiotec srl, Italy), Trichoderma viride ICC080, and / or Trichoderma oleracea HRU3 (BOTRY Botry Zen Ltd, NZ), and combinations thereof.

[0300] According to certain embodiments, the compounds and compositions of the present invention can be used in combination with one or more lipochito-oligosaccharides (LCO), chito-oligosaccharides (CO) and / or shell-based compounds. LCO, sometimes also referred to as symbiotic nodulation (Nod) signal (or Nod factor) or Myc factor, consists of a β-l,4-linked N-acetyl-D-glucosamine ("GlcNAc") residue oligosaccharide backbone and an N-linked fatty acyl chain condensed at the non-reducing end. As is understood in the art, LCOs differ in the number of GlcNAc residues in the backbone, the length and degree of saturation of the fatty acyl chain, and the substitution of reducing and non-reducing sugar residues. See, e.g., Denarie et al., Ann. Rev. Biochem. 65:503 (1996); Diaz et al., Mol. Plant Microbe Interactions 13:268 (2000); Hungria et al., Soil Biol. Biochem. 29:819 (1997); Hamel et al., Planta 232:787 (2010); and Prome et al., Pure & Appl. 70(1):55 (1998).

[0301] LCO (and its derivatives) may be contained or used in various forms of purity and may be used alone or in the form of a culture of LCO-producing bacteria or fungi. For example, (available from Bayer) contains a culture of bradyzobium rhizobium that produces LCO. Methods for providing substantially pure LCO include removing microbial cells from a mixture of LCO and microorganisms, or continuing to separate and purify the LCO molecule by LCO solvent phase separation, followed by HPLC chromatography, as described in U.S. Pat. No. 5,549,718. The purification effect can be improved by repeated high performance liquid chromatography, and the purified LCO molecule can be freeze-dried for long-term storage. The compositions and methods of the present disclosure may include analogs, derivatives, hydrates, isomers, salts and / or solvates of LCO. According to the present invention, LCO can be added to the composition in any suitable amount / concentration. For example, a composition according to the present invention comprises about 1x10 -20 M to about 1x10 -1 M LCO. The amount / concentration of the LCO may be an amount effective to impart positive traits or benefits to the plant, such as promoting growth and / or increasing yield of the plant to which the composition is applied. According to certain embodiments, the amount / concentration of the LCO may not be effective to increase the yield of the plant without the beneficial contribution of one or more other ingredients (e.g., CO and / or one or more pesticides) in the composition.

[0302] The compounds and compositions of the present invention may be used in combination with any suitable CO, and may also be used in combination with one or more LCOs. COs differ from LCOs in that they lack the pendant fatty acid chains characteristic of LCOs. COs, sometimes referred to as N-acetylchitosan oligosaccharides, are also composed of GlcNAc residues, but their side chain modifications make them different from the chitin molecule [(C8-H 13 NO5) n , CAS No. 1398-61-4] and chitosan molecules [(C5H 11 NO4) n, CAS number 9012-76-4]. See D'Haeze et al., Glycobiol. 12(6):79R (2002); Demont Caulet et al., Plant Physiol 120(1):83 (1999); Hanel et al., Planta 232:787 (2010); Muller et al., Plant Physiol 124:733 (2000); Robina et al., Tetrahedron 58:521-530 (2002); Rouge et al., Docking of Chitin Oligomers and Nod Factors on LysM-RLK Receptors in the Medicago-Rhizobium Symbiosis, in The Molecular Immunology of Complex Carbohydrates-3 (Springer Science, 2011); Van der Holst et al., Curr. Opin. Struc. Biol. 11:608 (2001); and Wan et al., Plant Physiol 124:733 (2000). Cell》21:1053(2009). CO can be obtained from any suitable source. For example, CO can be derived from LCO. For example, in one aspect, the composition according to the present invention comprises one or more CO derived from LCO, which can be obtained (isolated and / or purified) from the following strains: nitrogen-fixing rhizobium, bradyrhizobium (such as B. japonicum), bradyrhizobium wenxinzhong, rhizobium (such as pea rhizobium), Sinorhizobium (such as Sinorhizobium alfalfa) or mold (such as Glomus intraradicus). Alternatively, CO can also be synthetic. Methods for preparing recombinant CO are known in the art. For example, see Cottaz et al., Meth. Eng. 7(4):311(2005); Samain et al., Carbohydrate Res. 302:35(1997); and Samain et al., J. Biotechnol. 72:33(1999), the contents and disclosures of which are incorporated herein by reference.

[0303] CO (and its derivatives) may be included or used in various forms of purity and may be used alone or in the form of a culture of bacteria or fungi that produces CO. It should be understood that the compounds and compositions according to the present invention may be used in combination with hydrates, isomers, salts and / or solvates of CO. CO may be used in any suitable amount / concentration. For example, the composition according to the present invention may contain about 1x10 -20 M to about 1x10-1 The amount / concentration of CO may be an amount that is effective in imparting positive traits or benefits to plants, such as enhancing the soil microbial environment, nutrient absorption, or promoting growth and / or increasing yield of plants to which the composition is applied. According to certain embodiments, the amount / concentration of CO may not be effective in promoting plant growth without the beneficial contribution of one or more other components of the composition (e.g., LCO and / or one or more inoculants, biomacromolecules, nutrients, or pesticides).

[0304] The compounds and compositions of the present invention can be combined with one or more suitable chitin compounds, such as chitin, chitosan and isomers, salts and sols thereof. Chitin and chitosan are the main components of fungal cell walls and the exoskeletons of insects and crustaceans, and are composed of GlcNAc residues. Chitin and chitosan can be obtained commercially or prepared from insects, crustacean shells or fungal cell walls. Methods for preparing chitin and chitosan are well known in the art. For example, see U.S. Patent Nos. 4,536,207 (prepared from crustacean shells) and 5,965,545 (preparation and hydrolysis of commercial chitosan from crab shells); and Pochanavanich et al., Lett.Appl.35:17 (2002) (prepared from fungal cell walls). Deacetylated chitin and chitosan can have a degree of deacetylation ranging from less than 35% to greater than 90% and cover a wide range of molecular weights, e.g., low molecular weight chitosan oligomers with molecular weights less than 15 kD and chitosan oligomers with molecular weights between 0.5 and 2 kD; "practical grade" chitosan with molecular weights of about 15 kD; and high molecular weight chitosan with molecular weights up to 70 kD. Chitin and chitosan compositions for seed treatment are commercially available. Commercial products include (Plant Defense Boosters, Inc.) and BEYOND TM (Agrihouse, Inc.).

[0305] The compounds and compositions of the present invention may be combined with one or more suitable flavonoids, including but not limited to anthocyanidins, flavonoids, chalcones, coumarins, flavanones, flavanols, flavans and isoflavones, and their analogs, derivatives, hydrates, isomers, polymers, salts and solvates. Flavonoids are phenolic compounds whose general structure is two aromatic rings connected by three carbon bridges. Flavonoids are compounds known in the art. For example, see Jain et al., J. Plant Biochem. 11: 1 (2002); and Shaw et al., Environ. Microbiol. 11: 1867 (2006), the contents and disclosures of which are incorporated herein by reference. There are many flavonoid compounds on the market. Flavonoid compounds can be isolated from plants or seeds, as described in U.S. Patents 5,702,752, 5,990,291 and 6,146,668. Flavonoid compounds can also be produced by genetically engineered organisms, such as yeast. See Ralston et al., Plant Physiol 137:1375 (2005).

[0306] According to some embodiments, the compounds and compositions of the present invention can be used in combination with one or more flavanones, such as butin, eriodictyol, hesperetin, hesperidin, homoeriodictyol, isosakuranetin, naringenin, naringin, pinocembrin, poncir in), sakuranetin, sakuranin and / or sterubin; in combination with one or more flavanols, such as dihydrokaempferol and / or taxifolin; in combination with one or more flavans, such as one or more flavan-3-ols (e.g., catechin (C), catechin 3-gallate (Cg), epicatechin (EC), epigallocatechin (EGC), epicatechin 3-gallate (ECg ), epigallocatechin 3-gallate (EGCg), epifzelechin, fisetinidol, GC, GCg, guibourtinidol, mesquitol, robinetinidol, theaflavin-3-gallate, theaflavin-3'-gallate, flavin-3,3'-gallate, rhamnolide), flavan-4-ols (e.g., apiol and / or aloesol) and / or rhamnolide Alkane-3,4-diols (e.g., leucocyanidin, leucodelphinidin, leucofisetinidin, leucomalvidin, luecopelargonidin, leucopeonidin, leucorobinetinidin, melacacidin and / or teracacidin) and / or dimers, trimers, oligomers and / or polymers thereof (e.g., one or more proanthocyanidins);In combination with one or more isoflavones, for example, one or more isoflavones or flavonoid derivatives (e.g., biochanin A, daidzein, formononetin, genistein and / or glycitein), isoflavans (e.g., equol, ionchocarpane and / or laxifloorane), isoflavanediols, isoflavins (e.g., glabrene, haginin D and / or 2-methoxyjudaicin), coumestrols (e.g., coumestrol, plicadin, and / or wedelolactone), pterocarpans, roetonoids, newoflavonoids (e.g., calophyllolide, coutareagenin, dalbergichromene, dalbergin, nivetin), and / or pterocarpans (e.g., bitucarpin A, bitucarpin B, erybraedin A, erybraedin B, B. Erythrabyssin-Ⅱ, erythrabyssin-1, erycristagallin, glycinol, glyceollidins, glyceollins, glycyrrhizol, maackiain, medicarpin, morisianine, orientanol, phaseolin, pisatin, striatine, trifoliol olirhizin)), and combinations thereof. Flavonoid compounds and their derivatives may be included in the composition of the present invention in any suitable form, including but not limited to polymorphs and crystalline forms. According to the present invention, flavonoid compounds may be added to the composition in any suitable amount or concentration. The amount / concentration of flavonoids may be an effective amount that is beneficial to plants, which may be achieved indirectly through the activity of soil microorganisms or other means, such as improving plant nutrition and / or yield. According to certain embodiments, the amount / concentration of flavonoid compounds may not be effective in improving plant nutrition or yield without the beneficial contribution of one or more other components of the composition (such as LCO, CO and / or one or more pesticides). ;

[0307] The compounds and compositions of the present invention can be used in combination with one or more suitable non-flavonoid nodulation gene inducers, including but not limited to jasmonic acid ([1R-[1α,2β(Z)]]-3-oxo-2-(pentenyl)cyclopentaneacetic acid; JA), linoleic acid ((Z,Z)-9,12-octadecadienoic acid) and / or linolenic acid ((Z,Z,Z)-9,12,15-octadecatrienoic acid), and their analogs, derivatives, hydrates, isomers, polymers, salts and solvates. Jasmonic acid and its methyl jasmonate (MeJA), collectively referred to as jasmonates, are octadecyl compounds that occur naturally in certain plants (such as wheat), fungi (such as Botryodiplodia theobromae, Gibbrella fujikuroi), yeasts (such as Saccharomyces cerevisiae) and bacteria (such as Escherichia coli). Linoleic acid and linolenic acid may be produced during the biosynthesis of jasmonic acid. It is reported that jasmonic acid, linoleic acid and linolenic acid (and their derivatives) are inducers of rhizobia to express nodulation genes or produce LCO. For example, see Mabood et al., Plant Physiol. Biochem 44(11):759 (2006); Mabood et al., Agr. J. 98(2):289 (2006); Mabood et al., Field Crops Res. 95(2-3):412 (2006); and Mabood and Smith, Linoleic and linolenic acid induce the expression of nod genes in Bradyrhizobium japonicum USDA 3, Plant Biol. (2001).

[0308] Derivatives of jasmonic acid, linoleic acid, and linolenic acid that may be included or used in conjunction with the compounds and compositions of the present invention include esters, amides, glycosides, and salts thereof. Representative esters are those in which the carboxyl group of linoleic acid, linolenic acid, or jasmonic acid is replaced by a -COR group, wherein R is -OR 1 Group, where R 1 is: alkyl, such as C1-C8 unbranched or branched alkyl, such as methyl, ethyl or propyl; alkenyl, such as C2-C8 unbranched or branched alkenyl; alkynyl, such as C2-C8 unbranched or branched alkynyl; aryl, such as having 6 to 10 carbon atoms; or heteroaryl, such as having 4 to 9 carbon atoms, wherein the heteroatom in the heteroaryl can be, for example, N, O, P or S. Representative amides are those in which the carboxyl group of linoleic acid, linolenic acid or jasmonic acid is replaced by a -COR group, wherein R is NR 2 R 3 Group, where R 2 and R 3Each independently is: hydrogen; alkyl, such as C1-C8 unbranched or branched alkyl, for example, methyl, ethyl or propyl; alkenyl, such as C2-C8 unbranched or branched alkenyl; alkynyl, such as C2-C8 unbranched or branched alkynyl; aryl, for example, having 6 to 10 carbon atoms; or heteroaryl, for example, having 4 to 9 carbon atoms, wherein the heteroatom in the heteroaryl can be, for example, N, O, P or S. Esters can be prepared by known methods, such as acid-catalyzed nucleophilic addition, wherein carboxylic acid and alcohol react in the presence of a catalytic amount of a mineral acid. Amides can also be prepared by known methods, such as reacting carboxylic acid with an appropriate amine under neutral conditions in the presence of a coupling agent such as dicyclohexylcarbodiimide (DCC). Suitable salts of linoleic acid, linolenic acid and jasmonic acid include, for example, base addition salts and the like. Alkaline agents useful for preparing metabolically acceptable basic salts of these compounds include those derived from cations such as alkali metal cations (e.g., potassium and sodium) and alkaline earth metal cations (e.g., calcium and magnesium). These salts can be readily prepared by mixing solutions of linoleic acid, linolenic acid, or jasmonic acid with solutions of a base. These salts can precipitate from solution and be collected by filtration or can be recovered by other methods, such as evaporation of the solvent.

[0309] Non-flavonoid nodulation gene inducers can be used in combination with the compounds and compositions of the present invention and in any suitable amount / concentration. For example, the dosage / concentration of the non-flavonoid nodulation gene inducer can be an amount that can effectively impart positive traits or benefits to the plant, such as promoting the growth and / or increasing the yield of the plant to which the composition is applied. According to certain embodiments, the amount / concentration of the non-flavonoid nodulation gene inducer may not be able to effectively promote the growth of the plant without the beneficial contribution of one or more other ingredients in the composition (such as LCO, CO and / or one or more pesticides).

[0310] The compounds and compositions of the present invention can be combined with karrakins, including but not limited to 2H-furano[2,3-c]pyran-2-one, and analogs, derivatives, hydrates, isomers, polymers, salts and solvates thereof. Examples of biologically acceptable salts of karrakins include acid addition salts formed with biologically acceptable acids, examples of which include hydrochlorides, hydrobromides, sulfates or bisulfates, phosphoric acid or hydrogen phosphates, acetates, benzoates, succinates, fumarates, maleates, lactates, citrates, tartrates, gluconates; methanesulfonates, benzenesulfonates and p-toluenesulfonic acid. Other biologically acceptable metal salts may include alkali metal salts with bases, such as sodium and potassium salts. Karrakins can be used in any suitable amount / concentration and added to the compounds according to the present invention. For example, the dosage / concentration of karrakins can be an amount that can effectively impart positive traits or benefits to plants, promote the growth and / or increase the yield of plants to which the composition is applied. On the one hand, the amount / concentration of carahol may not be effective in promoting plant growth without the beneficial contribution of one or more other ingredients in the composition (such as LCO, CO and / or one or more pesticides).

[0311] The compounds and compositions of the present invention may be used in combination with one or more anthocyanidins and / or flavonoids, such as one or more cyanidin, delphinidin, malvidin, pelargonidin, peonidin, petunidin, flavonoids (e.g., apigenin, baicalein, chrysin, 7,8-dihydroxyflavone, diosmin (d iosmin), flavoxate, 6-hydroxyflavone, luteolin, scutellarein, tangeritin and / or wogonin and / or flavonols (e.g. amurensin, astragalin, azaleatin, azalein, fisetin, furanoflavonols galangin, galangin, gossypetin, 3-hydroxyflavone, hyperoside, icariin, isoquercetin, kaempferide, kaempferitrin, kaempferol, isorhamnetin, morin, myricetin, myricitrin, natsudaidain, pachypodol, pyranoflavonols quercetin, quericitin, rhamnazin, rhamnetin, robinin, rutin, spiraeoside, troxerutin and / or zanthorhamnin, and combinations thereof.

[0312] Compound and composition of the present invention can be used in combination with gluconolactone and / or its analog, derivative, hydrate, isomer, polymer, salt and / or solvate. Gluconolactone can be added to the composition according to the present invention with any suitable amount / concentration. For example, the amount / concentration of gluconolactone can be an effective amount of transmitting or giving positive characteristics or benefits to plants, such as promoting the growth and / or increasing yield of the plant applying the composition. In one aspect, if there is no beneficial contribution of one or more other components (such as LCO, CO and / or one or more pesticides) in the composition, the amount / concentration of gluconolactone may not effectively improve the growth and / or yield of plants.

[0313] The compounds and compositions of the present invention can be used in combination with one or more suitable nutrients and / or fertilizers, such as organic acids (e.g., acetic acid, citric acid, lactic acid, malic acid, taurine, etc.), macro minerals (e.g., phosphorus, calcium, magnesium, potassium, sodium, iron, etc.), trace minerals (e.g., boron, cobalt, chlorine, chromium, copper, fluorine, iodine, iron, manganese, molybdenum, selenium, zinc, etc.), vitamins (e.g., vitamin A, vitamin B complex (i.e., vitamin B1, vitamin B2, vitamin B3, vitamin B5, vitamin B6, vitamin B7, vitamin B8, vitamin B9, vitamin B10, vitamin B11, vitamin B12, vitamin B13, vitamin B14, vitamin B15, vitamin B16, vitamin B17, vitamin B18, vitamin B19, vitamin B20, vitamin B21, vitamin B22, vitamin B23, vitamin B24, vitamin B25, vitamin B26, vitamin B27, vitamin B28, vitamin B29, vitamin B30, vitamin B31, vitamin B32, vitamin B33, vitamin B34, vitamin B35, vitamin B36, vitamin B37, vitamin B38, vitamin B39, vitamin B40, vitamin B41, vitamin B42, vitamin B43, vitamin B44, vitamin B45, vitamin B46, vitamin B47, vitamin B48, vitamin B49, vitamin B50, vitamin B51, vitamin B52, vitamin B53, vitamin B54, vitamin B55, vitamin B56, vitamin B57, vitamin B58, vitamin B59, vitamin B60, vitamin B61, vitamin B62, vitamin B63, vitamin B64, vitamin B65, vitamin B66 12 , choline), vitamin C, vitamin D, vitamin E, vitamin K) and / or carotenoids (α-carotene, β-carotene, cryptoxanthin, lutein, lycopene, zeaxanthin, etc.), and combinations thereof. In one aspect, the compounds and compositions according to the present invention can be combined with macro- and micronutrients of plants or microorganisms, including phosphorus, boron, chlorine, copper, iron, manganese, molybdenum and / or zinc. According to certain embodiments, the compounds and compositions according to the present invention can be used in combination with one or more beneficial micronutrients. Non-limiting examples of micronutrients for the compositions described herein may include vitamins (e.g., vitamin A, vitamin B group (i.e., vitamin B5, vitamin B6, vitamin B7, vitamin B8, vitamin B9, vitamin B 12, choline), vitamin C, vitamin D, vitamin E, vitamin K, carotenoids (alpha-carotene, beta-carotene, cryptoxanthin, lutein, lycopene, zeaxanthin, etc.), macro minerals (such as phosphorus, calcium, magnesium, potassium, sodium, iron, etc.), trace minerals (such as boron, cobalt, chloride, chromium, copper, fluoride, iodine, iron, manganese, molybdenum, selenium, zinc, etc.), organic acids (such as acetic acid, citric acid, lactic acid, malic acid, taurine, etc.), and combinations thereof (BAYFOLAN secure, BAYFOLAN complete, BAYFOLAN energy, BAYFOLAN power from Aglukon, Germany). In a particular aspect, the composition may include phosphorus, boron, chlorine, copper, iron, manganese, molybdenum and / or zinc, and combinations thereof. For compositions comprising phosphorus, it is contemplated that any suitable source of phosphorus may be used. For example, the phosphorus may come from a phosphate rock source, such as monoammonium phosphate, diammonium phosphate, monocalcium phosphate, superphosphate, triple superphosphate and / or ammonium polyphosphate, an organic phosphorus source, or a phosphorus source that can be solubilized by one or more microorganisms, such as Penicillum bilaiae.

[0314] preparation

[0315] In another embodiment, the present invention relates to a plant protection agent in the form of a conventional formulation containing polymorph B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine of formula (I).

[0316] In a preferred embodiment of the invention, the crop protection agent contains more than 90% by weight and preferably more than 95% by weight of polymorph B of the compound of the formula (I), based on the total amount of all forms of the compound of the formula (I) present in the composition.

[0317] In a more preferred embodiment, the present invention relates to a suspension concentrate (SC) formulation comprising polymorph B of a compound of formula (I), one or more dispersants, one or more antifoaming agents, one or more biocides, one or more rheological additives, one or more antifreeze agents and / or one or more carriers.

[0318] In another embodiment, the present invention relates to an agrochemical formulation comprising polymorph B of a compound of formula (I), its use for foliar application; its use at low spray volumes; its use by unmanned aerial systems (UAS), unmanned guided vehicles (UGV) and tractors equipped with boom sprayers or rotating disc droplet applicators equipped with conventional nozzles and pulse width modulation spray nozzles; and its use for controlling agricultural diseases, especially on waxy leaves, and in particular, the present invention relates to an agrochemical composition with reduced drift, especially in spray application.

[0319] In one aspect, the invention relates to a formulation comprising:

[0320] a) polymorph B of a compound of formula (I) and one or more other active ingredients such as fungicides, bactericides, acaricides, nematicides, insecticides, biological control agents or herbicides,

[0321] b) one or more drift reducing agents,

[0322] c) one or more spreading agents,

[0323] d) one or more absorption enhancers,

[0324] e) one or more rainproof additives,

[0325] f) Other additives,

[0326] g) One or more carriers per volume (1 L or 1 kg).

[0327] In a preferred embodiment, b) is a vegetable oil or a vegetable oil ester or diester, and in another embodiment, component b) is a polymer drift reducer.

[0328] Drift reducer b)

[0329] Suitable drift reducing agents are polyethylene oxide, wherein the average molecular weight of the polymer is preferably from 500,000 to 12 million g / mol, more preferably from 750,000 to 10 million g / mol, and most preferably from 1 million to 8 million g / mol; hydroxypropyl guar gum, and vegetable oils, vegetable oil esters and vegetable oil diesters (including esters with glycerol and propylene glycol).

[0330] Particularly preferred are the methyl, ethyl, isopropyl, isobutyl, butyl, hexyl and ethylhexyl esters.

[0331] More preferred vegetable oils and vegetable oil esters are selected from methyl oleate, methyl palmitate, methyl rapeseed oil, isopropyl myristate, isopropyl palmitate, ethylhexyl palmitate, ethylhexyl oleate, a mixture of myristic acid / ethylhexyl laurate, ethylhexyl laurate, a mixture of caprylic acid / ethylhexyl caprate, diisopropyl adipate, propylene glycol dicopol, sunflower oil, rapeseed oil, corn oil, soybean oil, rice bran oil, olive oil, peanut oil, mixed caprylic and capric triglycerides, and mixed decanoyl and octanoyl glycerides.

[0332] Mineral oil is also suitable as a drift reducer.

[0333] Spreading agent c)

[0334] Suitable spreading agents are selected from the monoesters and diesters of metal salts of sulfosuccinates with branched or linear alcohols containing 1 to 10 carbon atoms, in particular alkali metal salts, more in particular sodium salts, most in particular sodium dioctyl sulfosuccinate; and silicone ethoxylates, for example organomodified polysiloxane / trisiloxane alkoxylates having the following CAS numbers: 27306-78-1, 67674-67-3, 134180-76-0, for example L77, 408, 806, S240, S278.

[0335] Other suitable spreading agents are ethoxylated diacetylenediols having 1 to 6 EO, for example 420 and 440, and ethoxylated propoxylated 3,5,5-trimethyl-1-hexanol, (CAS-No 204336-40-3), e.g. Vibrant.

[0336] Preferred is a polyether-modified heptamethyltrisiloxane, more preferably selected from the group comprising siloxane groups: poly(oxy-1,2-ethanediyl), α-methyl-ω-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propoxy] (CAS No. 27306-78-1), poly(oxy-1,2-ethanediyl), α-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propyl]-ω-hydroxy (CAS No. 67674-67-3), and a polymer of methylethylene oxide and ethylene oxide mono-3-1,3,3,3-tetramethyl-1-(trimethylsilyl)oxydisiloxanylpropyl ether (CAS No. 134180-76-0).

[0337] Preferably, the spreading agent is selected from dioctyl sodium sulfosuccinate, polyether-modified heptamethyl trisiloxane and ethoxylated diacetylene glycol.

[0338] Absorption enhancer (d)

[0339] Absorption enhancers may also be selected from the following compounds:

[0340] Other suitable absorption promoters are alcohol ethoxylates, preferably selected from ethoxylated alcohols, propoxy-ethoxylated alcohols, ethoxylated carboxylic acids, propoxy-ethoxylated carboxylic acids, or ethoxylated glycerol monoesters, diesters or triesters, which contain fatty acids having 8 to 18 carbon atoms and an average of 5 to 40 EO units. The ethoxylated or propoxy-ethoxylated alcohols or carboxylic acids are optionally further modified by adding methyl groups to the remaining alcohol functional groups (see "methyl-terminated"). The term "alcohols" according to d) refers to saturated or unsaturated branched or linear alcohols that may have 6 to 22 carbon atoms and optionally carry additional substituents (e.g. OH groups). The term "carboxylic acids" according to d) refers to saturated or unsaturated branched or linear carboxylic acids that may have 6 to 22 carbon atoms and optionally carry additional substituents (e.g. OH groups).

[0341] For example, suitable d) components are:

[0342] - ethoxylated linear and / or branched fatty alcohols (e.g. Clariant's X-type), which has 2-20 EO units;

[0343] - methyl-terminated ethoxylated linear and / or branched fatty alcohols (e.g. Clariant's XM type), which contains 2-20 EO units;

[0344] - Ethoxylated coconut alcohol (e.g. Clariant's Type C), which contains 2-20 EO units;

[0345] - Ethoxylated C12 / 15 alcohols (e.g. Croda's Type A), which contains 2-20 EO units;

[0346] - branched or linear propoxy-ethoxylated alcohols, such as Solvay's B / 848, Croda G5000, Levaco HOT 5902;

[0347] - Methyl terminated propoxy-ethoxylated fatty acids, such as Lion's OC0503M;

[0348] - alkyl ether citrate surfactants (e.g. Adsee CE series, Akzo Nobel);

[0349] -Alkyl polysaccharides (e.g. BASF's PG8107, PG8105; Croda 438, AL-2559, AL-2575);

[0350] - ethoxylated glycerol monoesters or diesters containing fatty acids having 8 to 18 carbon atoms and an average of 10 to 40 EO units (e.g. Croda's product line);

[0351] - castor oil ethoxylates containing on average 5 to 40 EO units (e.g. castor oil ethoxylates of Nouryon Series, Clariant EL series);

[0352] - ethoxylated oleic acid (e.g. A and AP), which contain 2-20 EO units;

[0353] - ethoxylated sorbitan fatty acid esters comprising fatty acids having 8 to 18 carbon atoms and an average of 10 to 50 EO units (e.g. T, Tween series).

[0354] Rainproof additives (e):

[0355] Suitable rainproof additives are acrylic-based emulsion polymers or polymer dispersions and styrene-based emulsion polymers or polymer dispersions, d) are aqueous polymer dispersions, whose Tg is -100°C to 30°C, preferably -60°C to 20°C, more preferably -50°C to 10°C, most preferably -45°C to 5°C, such as Acronal V215, Acronal 3612, Licomer ADH 205 and Atplus FA. Licomer ADH205 and Atplus FA are particularly preferred.

[0356] Preferably, the polymer is selected from acrylic polymers, styrene polymers, vinyl polymers and derivatives thereof, polyolefins, polyurethanes and natural polymers and derivatives thereof.

[0357] More preferably, the polymer is selected from acrylic polymers, styrene-butadiene copolymers, styrene-maleic anhydride copolymers, polyvinyl alcohol, polyvinyl acetate, partially hydrolyzed polyvinyl acetate, methyl vinyl ether-maleic anhydride copolymers, carboxyl-modified polyvinyl alcohol, acetoacetyl-modified polyvinyl alcohol, diacetone-modified polyvinyl alcohol and silicone-modified polyvinyl alcohol, isopropylene-maleic anhydride copolymers, polyurethanes, cellulose, gelatin, casein (caesin), oxidized starch, starch-vinyl acetate graft copolymers, hydroxyethyl cellulose, methyl cellulose, ethyl cellulose, carboxymethyl cellulose and acetyl cellulose.

[0358] Most preferably, the polymer is selected from a copolymer of acrylate and styrene, wherein the acrylate is selected from 2-ethylhexyl acrylate, butyl acrylate, sec-butyl acrylate, ethyl acrylate, methyl acrylate, acrylic acid, acrylamide, isobutyl acrylate, methyl methacrylate or a combination thereof. The styrene is selected from styrene, tert-butyl styrene, p-methyl styrene or a combination thereof.

[0359] In a preferred embodiment, as described above, the molecular weight of the polymer does not exceed 40,000, preferably does not exceed 10,000.

[0360] In a preferred embodiment, polymer D is an emulsion polymer as described in WO 2017 / 202684.

[0361] For many polymers, the glass transition temperature (Tg) is known and, if not otherwise defined, is determined in the present invention according to ASTM E1356-08 (2014) "Standard Test Method for Assignment of the Glass Transition Temperatures by Differential Scanning Calorimetry", wherein the sample is dried at 110°C for 1 hour before DSC to eliminate the effects of water and / or solvents, the DSC sample size is 10-15 mg, and the measurement is performed from -100°C to 100°C at 20°C / min under N2, wherein Tg is defined as the midpoint of the transition region.

[0362] Other additives (f)

[0363] f1 Suitable nonionic surfactants or dispersing aids f1) are all such substances which can be generally used for agricultural chemical agents. Preferably, polyethylene oxide-polypropylene oxide block copolymers, preferably having a molecular weight of more than 6,000 g / mol or a polyethylene oxide content of more than 45%, more preferably having a molecular weight of more than 6,000 g / mol and a polyethylene oxide content of more than 45%, polyoxyalkyleneamine derivatives, polyvinylpyrrolidone, copolymers of polyvinyl alcohol and polyvinylpyrrolidone, and copolymers of (meth)acrylic acid and (meth)acrylates. In the examples mentioned above, the selected species can optionally be phosphorylated, sulfonated or sulfated and neutralized with a base.

[0364] Possible anionic surfactants f1) are all such substances which are usually used in agricultural chemicals. Alkali metal salts, alkaline earth metal salts and ammonium salts of alkylsulfonic acids or alkylphosphonic acids and alkylarylsulfonic acids or alkylarylphosphonic acids are preferred. Another group of preferred anionic surfactants or dispersing aids are alkali metal salts, alkaline earth metal salts and ammonium salts of polystyrenesulfonic acid, salts of polyethylenesulfonic acid, salts of alkylnaphthalenesulfonic acids, salts of naphthalene-sulfonic acid-formaldehyde condensation products, salts of condensation products of naphthalenesulfonic acid, phenolsulfonic acid and formaldehyde, and salts of ligninsulfonic acid.

[0365] f2 rheology modifier is an additive that, when added to a formulation at a concentration that reduces gravity separation of dispersed active ingredients during storage, results in a significant increase in viscosity at low shear rates. For the purposes of this invention, low shear rates are defined as 0.1 s-1 and below, and a significant increase is greater than x2. Viscosity can be measured by a rotational shear rheometer.

[0366] Suitable rheology modifiers E2) are, for example:

[0367] - Polysaccharides including xanthan gum and hydroxyethylcellulose. Examples are G and 23, CX911 and 250 Series.

[0368] - Clays, including montmorillonite, bentonite, sepiolite, attapulgite, laponite, hectorite. Examples are R. Van B. 34, 38, CT, HC, EW, M100, M200, M300, S, M, W, 50. RD.

[0369] - fumed silica and precipitated silica, examples being 200, twenty two.

[0370] Preferred are xanthan gum, montmorillonite clay, bentonite and fumed silica.

[0371] f3 Suitable antifoaming substances e3) are all substances which can usually be used for this purpose in agrochemicals. Preference is given to silicone oils and silicone oil preparations. Examples are the silicone oils from Bluestar Silicones 426 and 432, from Wacker SRE and SC132, from Silchem Foam-Clear from Basildon Chemical Company Ltd From Momentive [dimethylsiloxane and silicone, CAS No. 63148-62-9] 1572 and 30. Preferably 1572.

[0372] Suitable antifreeze agents are all substances which can usually be used for this purpose in agricultural chemicals. Suitable examples are propylene glycol, ethylene glycol, urea and glycerol.

[0373] f5 Suitable other auxiliary agents e5) are selected from biocides, colorants, pH regulators, buffers, stabilizers, antioxidants, inert fillers, wetting agents, crystal growth inhibitors, micronutrients, for example:

[0374] Possible preservatives are all substances which can usually be used for this purpose in agricultural chemicals. Suitable examples of preservatives are preparations containing 5-chloro-2-methyl-4-isothiazolin-3-one [CAS No. 26172-55-4], 2-methyl-4-isothiazolin-3-one [CAS No. 2682-20-4] or 1,2-benzisothiazol-3(2H)-one [CAS No. 2634-33-5]. Examples which may be mentioned are D7 (Lanxess), CG / ICP(Dow), SPX (Thor GmbH) and GXL (Arch Chemicals).

[0375] Possible colorants are all substances which can usually be used for this purpose in agrochemicals. For example, titanium dioxide, carbon black, zinc oxide, blue pigments, brilliant blue FCF, red pigments and permanent red FGR may be mentioned.

[0376] Possible pH regulators and buffers are all substances which can usually be used for this purpose in agrochemicals. Mention may be made, for example, of citric acid, sulfuric acid, hydrochloric acid, sodium hydroxide, sodium hydrogen phosphate (Na2HPO4), sodium dihydrogen phosphate (NaH2PO4), potassium dihydrogen phosphate (KH2PO4), potassium hydrogen phosphate (K2HPO4).

[0377] Suitable stabilizers and antioxidants are all substances which can usually be employed for this purpose in agrochemicals. Preference is given to butylhydroxytoluene [3,5-di-tert-butyl-4-hydroxytoluene, CAS No. 128-37-0].

[0378] The carriers (g) are those usually used for this purpose in agrochemical formulations.

[0379] A carrier is a solid or liquid, natural or synthetic, organic or inorganic substance which is generally inert and can act as a solvent. The carrier generally improves the application of the compound to, for example, plants, plant parts or seeds. Examples of suitable solid carriers include, but are not limited to, ammonium salts, particularly ammonium sulfate, ammonium phosphate and ammonium nitrate, natural rock dusts, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, silica gel and synthetic rock dusts, such as finely divided silicon dioxide, alumina and silicates.

[0380] Examples of solid carriers that are commonly used to prepare granules include, but are not limited to, crushed and classified natural rocks such as calcite, marble, pumice, sepiolite and dolomite, synthetic particles of inorganic and organic powders, and particles of organic materials such as paper, sawdust, coconut shells, corn cobs and tobacco stalks.

[0381] Preferred solid carriers are selected from clay, talc and silica.

[0382] Examples of suitable liquid carriers include, but are not limited to, water, organic solvents, and combinations thereof. Examples of suitable solvents include polar and non-polar organic chemical liquids, such as from the following categories:

[0383] - alcohols and polyols (which may also optionally be substituted, etherified and / or esterified, for example ethanol, propanol, butanol, benzyl alcohol, cyclohexanol or ethylene glycol, 2-ethylhexanol),

[0384] - ethers, such as dioctyl ether, tetrahydrofuran, isosorbide dimethyl ether, solketal, cyclopentyl methyl ether, solvents from the Dowanol product line provided by Dow, such as Dowanol DPM, anisole, phenethyl ether, dimethyl polyethylene glycol of different molecular weight grades, dimethyl polypropylene glycol of different molecular weight grades, dibenzyl ether

[0385] - ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, cycloheptanone, acetophenone, propiophenone),

[0386] - lactic acid esters, such as methyl lactate, ethyl lactate, propyl lactate, butyl lactate, 2-ethylhexyl lactate,

[0387] - (poly)ethers, such as polyethylene glycol of different molecular weight grades, polypropylene glycol of different molecular weight grades,

[0388] - unsubstituted and substituted amines,

[0389] - amides (for example dimethylformamide, or N,N-dimethyllactamide, or N-formylmorpholine, or fatty acid amides, such as N,N-dimethyldecylamide or N,N-dimethyldodecanamide) and esters thereof,

[0390] - lactams (for example 2-pyrrolidone, or N-alkylpyrrolidone, for example N-methylpyrrolidone, or N-butylpyrrolidone, or N-octylpyrrolidone, or N-dodecylpyrrolidone or N-methylcaprolactam, N-alkylcaprolactam),

[0391] - lactones (for example γ-butyrolactone, γ-valerolactone, δ-valerolactone or α-methyl γ-butyrolactone),

[0392] - sulfones and sulfoxides (for example dimethyl sulfoxide),

[0393] - nitriles, for example linear or cyclic alkylnitriles, in particular acetonitrile, cyclohexanenitrile, octanonitrile, dodecanonitrile,

[0394] - linear and cyclic carbonates, for example diethyl carbonate, dipropyl carbonate, dibutyl carbonate, dioctyl carbonate or ethylene carbonate, propylene carbonate, butylene carbonate, glycerol carbonate,

[0395] The most preferred carrier is water.

[0396] These spray liquors are applied by customary methods, ie for example by spraying, pouring or injection, in particular by spraying, most in particular by UAV spraying.

[0397] A. Methods and Abbreviations

[0398] A-1. method

[0399] Unless otherwise stated, all data forming part of this application have been prepared according to the methods described below. The samples used for the measurements were used directly without any further sample preparation.

[0400] Determination of LogP value

[0401] The measurement of the LogP values ​​provided herein was carried out in accordance with EEC directive 79 / 831 Annex V.A8 by HPLC (high performance liquid chromatography) on a reverse phase column, using a method determined by LC-UV measurement in the acidic range using 0.1% formic acid in water and acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0402] Calibration was performed using linear alkan-2-ones (having 3 to 16 carbon atoms) with known LogP values ​​(LogP values ​​were measured using retention times by linear interpolation between adjacent alkanones). The λmax value was determined using the UV spectrum from 200 nm to 400 nm and the peak of the chromatographic signal.

[0403] 1 H-NMR data

[0404] The selected embodiments provided herein 1 H-NMR data 1 H-NMR peaks are shown in the form of a table. For each signal peak, the d value in ppm is listed, and the signal intensity is listed in parentheses. The d value-signal intensity pairs are separated by semicolons.

[0405] Thus, the peak list for an instance takes the following form:

[0406] d1 (intensity 1); d2 (intensity 2); ...; di (intensity i); ...; dn (intensity n)

[0407] The intensity of the sharp signal is related to the height of the signal in the printed NMR spectrum example in centimeters and shows the actual relationship of the signal strength. Broad peak signals can show multiple peaks or signal centers and their relative intensities compared to the strongest signal in the spectrum.

[0408] For calibration 1 For the chemical shift of H spectra we utilize the chemical shift of tetramethylsilane and / or the solvent used, especially in the case of spectra measured in DMSO. Therefore, in the NMR peak list, the tetramethylsilane peak may, but need not, appear.

[0409] 1 The listing of H-NMR peaks is similar to the conventional 1 H-NMR printouts, therefore, usually contain all the peaks listed in a conventional NMR analysis.

[0410] In addition, as traditional 1 H-NMR print, which may show signals for the solvent, for stereoisomers of the target compound (which is also a subject of the present invention) and / or for impurity peaks.

[0411] To show the signals of compounds in the δ range of solvent and / or water, typical solvent peaks, such as the DMSO peak and the water peak in DMSO-D6, are shown in our 1 H-NMR peaks are listed and usually have average high intensities.

[0412] Peaks of stereoisomers of a target compound and / or peaks of impurities typically have on average lower intensities than peaks of the target compound (eg, having a purity of >90%).

[0413] These stereoisomers and / or impurities may be typical for a particular preparation process. Therefore, their peaks can help identify the reproducibility of the preparation process by means of a "by-product fingerprint".

[0414] Experts who calculate the peak of the target compound by known methods (MestreC, ACD simulation, and using empirically estimated expected values) can optionally use additional intensity filters to separate the peak of the target compound as needed. This separation is similar to traditional 1 Picking of relevant peaks under H-NMR analysis.

[0415] Further details of the interpretation of NMR data with peak lists can be found in the publication "Citation of NMR Peaklist Data within Patent Applications" in Research Disclosure Database Number 564025.

[0416] Separation of enantiomers

[0417] The enantiomer separation of the racemate is carried out by preparative supercritical fluid chromatography using supercritical carbon dioxide as mobile phase and lower alcohols as modifiers, more preferably methanol, ethanol or isopropanol, in a ratio of 15 to 30% by volume. The total flow rate is in the range of 70-100 mL / min and the chromatographic separation is carried out at a temperature in the range of 30° C. to 50° C. and a back pressure in the range of 70 bar to 130 bar in one of the following commercially available and known isothermal chiral stationary phases:

[0418] -ChiralPak IA, 250x20mm, Daicel Chemical Industries.

[0419] -Lux Amylose-1, 250x21.2mm 5μm, Axia loading from Phenomenex.

[0420] -Lux Cellulose-1, 250x21.2mm 5μm, Axia loading from Phenomenex.

[0421] -Lux i-Cellulose-5, 250x21.2mm 5μm, Axia loading from Phenomenex.

[0422] XRPD

[0423] X-ray diffraction patterns were recorded at room temperature using an XRD diffractometer X`Pert PRO (PANalytical) and STOE STADI-P (Cu Kα1 radiation, wavelength 1.5406). All X-ray reflections are quoted as °2θ (θ) values ​​(peak maximum) with a resolution of ±0.2°.

[0424] Raman

[0425] Raman spectra were recorded at room temperature using a Bruker FT-Raman spectrophotometer (model MultiRam). The resolution was 2 cm -1 The measurements are carried out in glass bottles or aluminium pans.

[0426] IR

[0427] IR-ATR spectra were recorded at room temperature using a Bruker FT-IR spectrophotometer Tensor 37 or Alpha with a universal diamond ATR setup. The resolution was 2 cm -1 .

[0428] TGA

[0429] TGA thermograms were recorded using a Perkin-Elmer thermobalance (model TGA 8000) and a Mettler Toledo thermobalance (model TGA / DSC3+). Measurements were made using an open platinum pan (Perkin Elmer) and a perforated aluminum pan (Mettler) at 10 Kmin -1 The heating rate was 2.13° and the flowing gas was nitrogen.

[0430] B. Example

[0431] B-1. Synthesis

[0432] Preparation Example 1: (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (I) [2446130-20-5]

[0433] Step 1: Preparation of N-[(2RS)-1-chloro-3-(2-chloro-4-methylphenyl)propan-2-yl]-3-(3-chloro-2-fluorophenoxy)-6-methylpyridazine-4-carboxamide [2446133-45-3]

[0434] Under argon, 3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazine-4-carboxylic acid [2435607-79-5] (175g, 619mmol) and (2RS)-1-chloro-3-(2-chloro-4-methylphenyl)propan-2-amine hydrochloride (1:1) [2446132-78-9] (262g, 928mmol) were suspended in 3L of dichloromethane, and then propanephosphonic anhydride (682mL, 2290mmol) was slowly added over 10 minutes, N, N-diisopropylethylamine (393mL, 2250mmol) was added dropwise, and the reaction was stirred at room temperature for 18 hours. The reaction mixture was then poured into 1.5L of saturated sodium bicarbonate aqueous solution and 1L of water was added. The mixture was extracted twice with 500mL of dichloromethane. The combined organic layer was dried over sodium sulfate, filtered and evaporated. The product was purified by column chromatography using a 3 kg silica gel column (solid deposits) with an elution gradient of heptane / ethyl acetate 100 / 0 to 0 / 100. After evaporation of the solvent, 250 g (100% purity, 83% yield) of the title compound were recovered as a solid.

[0435] Step 2:Preparation of N-[(2RS)-1-chloro-3-(2-chloro-4-methylphenyl)propan-2-yl]-3-(3-chloro-2-fluorophenoxy)-N'-hydroxy-6-methylpyridazine-4-carboxamidine [2446133-13-5]

[0436] To a solution of N-[(2RS)-1-chloro-3-(2-chloro-4-methylphenyl)propan-2-yl]-3-(3-chloro-2-fluorophenoxy)-6-methylpyridazine-4-carboxamide [2446133-45-3] (249 g, 515 mmol) in toluene (3 L) was added phosphorus pentachloride (215 g, 1030 mmol). The reaction mixture was stirred at 75 °C for 1 h and then concentrated under reduced pressure. The residue was dissolved in 1,4-dioxane (1.2 L) and a solution of hydroxylamine (681 g, 10.3 mol, 50% aqueous solution) diluted in 1,4-dioxane (2.8 L) at 15 °C was added to the reaction mixture over 30 minutes. After stirring at room temperature for 16 h, the reaction mixture was diluted with water (6 L) and then 1.6 L of hydrochloric acid 6M was slowly added. The aqueous phase was extracted with ethyl acetate (4×750 mL). The organic extracts were washed with brine (1 L), dried over sodium sulfate, filtered and concentrated under reduced pressure. The solvent was evaporated to give 309 g (80% purity, 96% yield) of the title product as a yellow oil.

[0437] Step 3: Preparation of (5RS)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine [2446129-82-2]

[0438] To a solution of N-[(2RS)-1-chloro-3-(2-chloro-4-methylphenyl)propan-2-yl]-3-(3-chloro-2-fluorophenoxy)-N'-hydroxy-6-methylpyridazine-4-carboximidamide [2446133-13-5] (278 g, 474 mmol) in acetonitrile (5 L) and water (50 mL) was added potassium tert-butoxide (173 g, 830 mmol). The reaction mixture was stirred at 45 °C for 45 min. The reaction mixture was diluted with water (1 L) and the acetonitrile was evaporated under vacuum. The resulting mixture was diluted with water (8 L) and extracted with ethyl acetate (3 x 1.5 L). The combined organic layers were washed with brine (2 x 1 L), dried over magnesium sulfate, filtered and concentrated. The residue was first purified by column chromatography using a 3 kg silica gel column (solid deposit), with an elution gradient of dichloromethane 100 to dichloromethane / ethyl acetate 70 / 30, and then by column chromatography using a 1.5 kg silica gel column solid deposit for secondary purification, with a gradient of heptane 100 to ethyl acetate 100. The collected fractions were concentrated to give an orange viscous solid. The solid was ground in 500 mL heptane at 50 ° C for 2 hours, then filtered to give 115 g (99% purity, 50% yield) of the title compound.

[0439] Separation of enantiomers

[0440] The separation on the preparative scale was carried out on a device SFC-PICLAB Hybrid 10-150 from Pic Solution with UV detection in the range between 210 nm and 280 nm, preferably between 220 nm and 254 nm.

[0441] (5RS)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (mixture of diastereomers) (17 g, 99% purity) was separated by preparative supercritical fluid chromatography to give (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (mixture of diastereomers) pyridazine-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (8.71 g, 100% purity) and (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (8.77 g, 100% purity).

[0442] Column: ChiralPak IA, 250x20mm; eluent A: CO2; eluent B: methanol; isocratic 25%

[0443] Analytical chiral HPLC. Column ChiralPak IB N-5 150x2,1 5μm; eluent A: water + 0.1% HCOOH; eluent B: acetonitrile + 0.1% HCOOH; isocratic 45:55A / B; flow rate: 0.175ml / min; UV: 220nm; oven: 25℃

[0444] (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine: R t =12.33min; Optical rotation: +79.7° (c=1.21, CDCl3, 25°C), concentration c is expressed in g / 100mL

[0445] (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (I): R t =13.09min; optical rotation: -81.4° (c=1.16, CDCl3, 25°C), concentration c is expressed in g / 100mL

[0446] LogP: 3.88

[0447] 1 H-NMR (600.2 MHz, CDCl3):

[0448] δ=7.9188(5.3); 7.3551(0.6); 7.3490(0.7); 7.3445(1.1); 7.3389(1.2); 7.3333(0 .7);7.3280(0.7);7.2619(5.8);7.1515(3.6);7.1452(2.0);7.1397(2.8);7.1100( 2.3); 7.1090(2.3); 7.0607(2.1); 7.0479(2.3); 6.7461(1.2); 6.7449(1.2); 6.7334(1.1); 6.7322(1.1); 6.0010(1.2); 4.2055(1.0); 4.1999(1.1); 4.1873(1.2); 4.181 7(1.2); 4.0168(0.4); 4.0118(0.5); 4.0075(0.6); 4.0045(0.6); 4.0016(0.6); 3.9973(0.6); 3.9923(0.4); 3.8732(1.3); 3.8641(1.2); 3.8550(1.2); 3.8459(1.1); 3.1 400(0.9); 3.1316(0.9); 3.1175(1.0); 3.1091(1.0); 2.8832(1.1); 2.8676(1.1); 2.8608(1.0); 2.8452(0.9); 2.6415(16.0); 2.1863(11.5); 1.5862(2.0); 0.0000(7.7)

[0449] B-2. (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)- Polymorph B of 5,6-dihydro-4H-1,2,4-oxadiazine

[0450] B-2-1. Preparation of polymorph B

[0451] The compound of formula (I) was dissolved in each solvent (given in Table 5) at the respective boiling temperature. The solution was filtered and divided into four, three or two portions (depending on the solvent used, if any).

[0452] Store each portion separately in

[0453] a) At room temperature

[0454] b) In a refrigerator (4°C to 7°C)

[0455] c) In a freezer (-20℃ to -18℃)

[0456] Until dry,

[0457] d) Optionally, adding an antisolvent.

[0458] Table 5: Solvents used for Form B

[0459]

[0460]

[0461] Examples 4 to 16 in Table 5 yielded polymorph B. The resulting polymorph B crystals were isolated and analyzed by X-ray powder diffraction (XRPD), Raman spectroscopy, and infrared spectroscopy.

[0462] B-3. (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)- Polymorph A of 5,6-dihydro-4H-1,2,4-oxadiazine

[0463] B-3-1. Preparation of polymorph A

[0464] Method for preparing polymorph A

[0465] In order to obtain crystals of polymorph A, temperature-dependent X-ray powder diffraction (XRPD) experiments were performed, in which recrystallization was allowed at different temperatures. Phase transitions were observed at 60°C upon heating and at 40°C upon cooling. The X-ray diffraction pattern of polymorph A was observed at 75°C.

[0466] The resulting crystals of polymorph A were isolated and analyzed by X-ray powder diffraction (XRPD).

[0467] C. (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methyl) Properties of Polymorph B of (Benzyl)-5,6-dihydro-4H-1,2,4-oxadiazine

[0468] C-1. Formulation Examples

[0469] The formulation of the compound of formula (I) in polymorph B was prepared as a suspension concentrate (SC) formulation according to the formulation in Table 6. The formulation was prepared by the following method: first, a 2% gel of Rhodopol 23 was prepared in water containing a biocide. The remaining components were mixed in the following order under stirring: water, antifreeze, defoamer and dispersant until dissolved, and then the powder of polymorph B of the compound of formula (I) was added, dispersed by mixing, and ground in a bead mill to obtain a particle size (Dv50) of 1 to 10 microns. 2% Rhodopol 23 gel was added to the ground dispersion under low shear mixing to obtain a SC formulation. The formulation was then tested for stability by storing samples at 70°C and 80°C.

[0470] Table 6: SC formulation formula 1

[0471]

[0472]

[0473] Physical properties were determined by visual inspection of the samples, micromorphology was determined by diluting the SC formulation to about 1% and observing the aggregation state and size of the crystals of the polymorph B of the compound of formula (I) of the present invention. Dilution stability (also known as suspension) was determined by the following method: 100 ml of a 1% v / v dispersion was prepared by mixing in CIPAC C water (hardness 500 ppm) (www.cipac.org MT18.1) in a graduated cylinder with a special narrow end at the bottom to visualize the volume of any precipitate after 1 hour. The measurement was carried out at room temperature.

[0474] Table 7: Stability of formulation 1

[0475] test initial 1 week @70℃ 5 days @80℃ Micro Dispersed particles Dispersed particles Dispersed particles Appearance Fluid Suspension Fluid Suspension Fluid Suspension Suspension (1%, 1h) <![CDATA[Trace # > <![CDATA[Trace # > <![CDATA[Trace # >

[0476] Trace # Refers to particles smaller than 0.1 mL that can be observed in a sample volume of 100 mL

[0477] The temperatures applied in Table 7 are much higher than those used in the standard procedure where the samples are subjected to a temperature of 54°C for 2 weeks.

[0478] The results in Table 7 show that there is no difference in the microscopic probe in terms of appearance and suspension after one week at 70°C and after 5 days at 80°C. In particular, with regard to suspension, the SC formulation comprising polymorph B of the compound of formula (I) showed only traces (less than 0.1 mL) of particles even after subjecting the probe to temperatures of 70°C (for one week) and 80°C (for 5 days). These temperatures are above the transition temperature range of 49°C to 66°C. No transition to polymorph A was observed.

[0479] These results show that polymorph B exhibits surprisingly high stability even when subjected to temperatures above the transition temperature range of polymorph B to polymorph A for several days. Thus, SC formulations comprising polymorph B of the compound of formula (I) surprisingly have high stability, preferably high dilution stability, more preferably high suspensibility, which is of particular relevance since polymorphic transitions are expected to lead to instability of SC formulations.

[0480] C-2. Serum experiment

[0481] As shown in Table 8, the compound of formula (I) was suspended in the corresponding solvent and stirred at 0°C, 40°C (Mya4 stirrer station, 250 U / min) and 80°C (Reacti-Therm III, stirring level 6). After three to eight days, an additional amount of solvent was added to the suspension. In two experiments, the other substances were added after four days. After eight days, the suspension was dried under ambient conditions. The resulting crystals were isolated and analyzed by X-ray powder diffraction (XRPD) spectrum, DSC and TGA. Figure 3a shows the XRPD after slurry experiment 3.

[0482] Table 8:

[0483]

[0484] * 4 days later, add 83 mg

[0485] ** 4 days later, add 272 mg

Claims

1. Crystalline Form B of the Compound of Formula (I) Its X-ray powder diffraction pattern at 25° C. and Cu—Kα1 radiation shows at least the following reflections, quoted as 2θ values ​​±0.2°: 20.2, 23.3 and 25.

1.

2. Form B of the compound of claim 1, which exhibits in its X-ray powder diffraction pattern at 25°C and Cu-Ka1 radiation at least the following reflections, quoted as 2θ values ​​±0.2°: 20.2, 23.3, 25.1, 14.5 and 19.

4.

3. Form B of the compound of claim 1, which exhibits in its X-ray powder diffraction pattern at 25°C and Cu-Kα1 radiation at least the following reflections, quoted as 2θ values ​​±0.2°: 20.2, 23.3, 25.1, 14.5, 19.4, 23.4 and 10.

6.

4. Form B of the compound of formula (I) according to claim 1, which exhibits at least the following bands in the Raman spectrum (peak maximum, in cm -1 ):98, 112 and 1585.

5. Form B of the compound of formula (I) according to claim 1, which exhibits at least the following bands in the Raman spectrum (peak maximum, in cm -1 ): 98, 112, 1585, 1279 and 2925.

6. Form B of the compound of formula (I) according to claim 1, which exhibits at least the following bands in the Raman spectrum (peak maximum, in cm -1 ): 98, 112, 1585, 1279, 2925, 688 and 1609.

7. A method for preparing the crystalline form B according to any one of claims 1 to 6, comprising the following steps: a) diluting the compound of formula (I) in a suitable solvent or solvent mixture, b) heating the composition of step a) to a temperature of at least 70° C., and c) cooling the solution from step b) to a temperature below 20°C.

8. A composition comprising the polymorph B according to any one of claims 1 to 6.

9. The composition of claim 8, wherein the composition comprises at least a) one or more drift reducing ingredients, b) one or more spreading agents, c) one or more absorption enhancers, d) one or more rainfast additives, e) optional other adjuvants and / or f) one or more carrier extensions.

10. The composition of claim 8 or 9, wherein the composition is a suspension concentrate formulation.

11. A plant protection agent comprising the crystalline form B of formula (I) according to any one of claims 1 to 6 or the composition according to any one of claims 8 to 10.

12. The plant protection agent according to claim 11, further comprising one or more other active substances selected from the group consisting of herbicides, insecticides, miticides, fungicides, safeners and / or plant growth regulators.

13. Use of the polymorph B according to any one of claims 1 to 6 for preparing a composition or a plant protection agent, said composition or plant protection agent preferably having a high stability, more preferably having a high stability at a temperature above the transition temperature.

14. Use of the polymorph B according to any of claims 1 to 6, or a formulation according to any of claims 8 to 10, or a plant protection agent according to claim 11 or 12 for controlling unwanted microorganisms.

15. A method for controlling unwanted microorganisms, wherein the polymorph B according to any of claims 1 to 6, the formulation according to any of claims 8 to 10 or the plant protection agent according to claim 11 or 12 is applied to useful plants.

16. Crystalline Form A of the Compound of Formula (I) Its X-ray powder diffraction pattern at 25° C. and Cu—Kα1 radiation shows at least the following reflections, quoted as 2θ values ​​±0.2°: 16.9, 19.8 and 24.

5.

17. Form A of the compound of claim 16, which exhibits in its X-ray powder diffraction pattern at 25°C and Cu-Kα1 radiation at least the following reflections, quoted as 2θ values ​​±0.2°: 16.9, 19.8, 24.5, 14.2 and 24.

7.

18. Form A of the compound of claim 16, which exhibits in its X-ray powder diffraction pattern at 25°C and Cu-Kα1 radiation at least the following reflections, quoted as 2θ values ​​±0.2°: 16.9, 19.8, 24.5, 14.2, 24.7, 20.8 and 21.8.

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